CN112334567A - 气味剂仲醇及其组合物 - Google Patents
气味剂仲醇及其组合物 Download PDFInfo
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- CN112334567A CN112334567A CN201980036627.3A CN201980036627A CN112334567A CN 112334567 A CN112334567 A CN 112334567A CN 201980036627 A CN201980036627 A CN 201980036627A CN 112334567 A CN112334567 A CN 112334567A
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- formula
- hex
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- pent
- alcohol
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- 239000000203 mixture Substances 0.000 title claims abstract description 193
- 239000003205 fragrance Substances 0.000 title claims abstract description 75
- 150000003333 secondary alcohols Chemical class 0.000 title description 2
- 239000000796 flavoring agent Substances 0.000 claims abstract description 56
- 235000019634 flavors Nutrition 0.000 claims abstract description 56
- 150000001298 alcohols Chemical class 0.000 claims abstract description 43
- 230000000873 masking effect Effects 0.000 claims abstract description 43
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 claims abstract description 38
- 230000001877 deodorizing effect Effects 0.000 claims abstract description 35
- -1 2-pentyl Chemical group 0.000 claims description 262
- 150000001875 compounds Chemical class 0.000 claims description 130
- 125000004432 carbon atom Chemical group C* 0.000 claims description 84
- 238000003786 synthesis reaction Methods 0.000 claims description 67
- 230000015572 biosynthetic process Effects 0.000 claims description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 150000002576 ketones Chemical class 0.000 claims description 54
- 230000010933 acylation Effects 0.000 claims description 41
- 238000005917 acylation reaction Methods 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 230000029936 alkylation Effects 0.000 claims description 21
- 238000005804 alkylation reaction Methods 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 10
- 125000006039 1-hexenyl group Chemical group 0.000 claims description 10
- 125000006023 1-pentenyl group Chemical group 0.000 claims description 10
- 125000006017 1-propenyl group Chemical group 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 10
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 8
- 125000006040 2-hexenyl group Chemical group 0.000 claims description 8
- 125000006024 2-pentenyl group Chemical group 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000006041 3-hexenyl group Chemical group 0.000 claims description 8
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 8
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- HTLILIPBZXKCQU-UHFFFAOYSA-N 2,3,3,5,5,6-hexamethylhepta-1,6-dien-4-ol Chemical compound CC(=C)C(C)(C)C(O)C(C)(C)C(C)=C HTLILIPBZXKCQU-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- AZKNCTAVLPVLFM-UHFFFAOYSA-N 2,3,3,5,5,6-hexamethylheptan-4-ol Chemical compound CC(C)C(C)(C)C(O)C(C)(C)C(C)C AZKNCTAVLPVLFM-UHFFFAOYSA-N 0.000 claims description 2
- HCFZYLDKEMFOCF-UHFFFAOYSA-N 2,3,3,6,7-pentamethylocta-1,6-dien-4-ol Chemical compound CC(=C)C(C(CC(=C(C)C)C)O)(C)C HCFZYLDKEMFOCF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 96
- 239000003921 oil Substances 0.000 description 89
- 235000019198 oils Nutrition 0.000 description 89
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 125000005188 oxoalkyl group Chemical group 0.000 description 21
- 239000003039 volatile agent Substances 0.000 description 20
- 150000001299 aldehydes Chemical class 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000012279 sodium borohydride Substances 0.000 description 14
- 229910000033 sodium borohydride Inorganic materials 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 244000203593 Piper nigrum Species 0.000 description 9
- 235000008184 Piper nigrum Nutrition 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 description 8
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 8
- 235000002566 Capsicum Nutrition 0.000 description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- 239000006002 Pepper Substances 0.000 description 8
- 235000016761 Piper aduncum Nutrition 0.000 description 8
- 235000017804 Piper guineense Nutrition 0.000 description 8
- 229940022663 acetate Drugs 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000002304 perfume Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 7
- 241000721662 Juniperus Species 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 229940041616 menthol Drugs 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- VBZRWZVYUDHMDL-UHFFFAOYSA-N 4,4,5-trimethylhex-5-en-3-one Chemical compound CCC(=O)C(C)(C)C(C)=C VBZRWZVYUDHMDL-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000005882 aldol condensation reaction Methods 0.000 description 6
- 235000020971 citrus fruits Nutrition 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 241000207199 Citrus Species 0.000 description 5
- 241000402754 Erythranthe moschata Species 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 5
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 5
- DHSJZHJJRMUNML-UHFFFAOYSA-N 2,3,3-trimethylhepta-1,5-dien-4-ol Chemical compound CC=CC(O)C(C)(C)C(C)=C DHSJZHJJRMUNML-UHFFFAOYSA-N 0.000 description 4
- PKMNOWXMJMESLE-UHFFFAOYSA-N 2,3,3-trimethylnon-1-en-4-one Chemical compound CC(=C)C(C(CCCCC)=O)(C)C PKMNOWXMJMESLE-UHFFFAOYSA-N 0.000 description 4
- RHFJWJGFEWFQAO-UHFFFAOYSA-N 2,3,3-trimethyloct-1-en-4-one Chemical compound CC(=C)C(C(CCCC)=O)(C)C RHFJWJGFEWFQAO-UHFFFAOYSA-N 0.000 description 4
- WYDFAHTYMZXGHN-UHFFFAOYSA-N 2,4,4,5-tetramethylhex-5-en-3-ol Chemical compound CC(C)C(C(C(=C)C)(C)C)O WYDFAHTYMZXGHN-UHFFFAOYSA-N 0.000 description 4
- MWNJHTYVAYIQHN-UHFFFAOYSA-N 3,3,4-trimethylpent-4-en-2-ol Chemical compound CC(O)C(C)(C)C(C)=C MWNJHTYVAYIQHN-UHFFFAOYSA-N 0.000 description 4
- MQJUHFWPBZLKFV-UHFFFAOYSA-N 3,3,4-trimethylpentan-2-one Chemical compound CC(C)C(C)(C)C(C)=O MQJUHFWPBZLKFV-UHFFFAOYSA-N 0.000 description 4
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- KAZITODGZVBFML-UHFFFAOYSA-N 4,4,5-trimethylhex-5-en-3-ol Chemical compound CC(C(CC)O)(C(=C)C)C KAZITODGZVBFML-UHFFFAOYSA-N 0.000 description 4
- 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
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 4
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 4
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- IPWBXORAIBJDDQ-UHFFFAOYSA-N methyl 2-hexyl-3-oxocyclopentane-1-carboxylate Chemical compound CCCCCCC1C(C(=O)OC)CCC1=O IPWBXORAIBJDDQ-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- FRISMOQHTLZZRP-UHFFFAOYSA-N nerol oxide Chemical compound CC(C)=CC1CC(C)=CCO1 FRISMOQHTLZZRP-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
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- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
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- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
- RDYCDXUGQVOHRJ-UHFFFAOYSA-N 2,3,3,5-tetramethylhept-1-en-4-ol Chemical compound CC(=C)C(C(C(CC)C)O)(C)C RDYCDXUGQVOHRJ-UHFFFAOYSA-N 0.000 description 3
- RDGUPBKHGYFVMK-UHFFFAOYSA-N 2,3,3,5-tetramethylhept-1-en-4-one Chemical compound CC(=C)C(C(C(CC)C)=O)(C)C RDGUPBKHGYFVMK-UHFFFAOYSA-N 0.000 description 3
- WJGYCXHFJVYOCO-UHFFFAOYSA-N 2,3,3-trimethylhept-1-en-4-ol Chemical compound CC(=C)C(C(CCC)O)(C)C WJGYCXHFJVYOCO-UHFFFAOYSA-N 0.000 description 3
- NINDFMBMSJQFKI-UHFFFAOYSA-N 2,3,3-trimethylhept-1-en-4-one Chemical compound CCCC(=O)C(C)(C)C(C)=C NINDFMBMSJQFKI-UHFFFAOYSA-N 0.000 description 3
- ITSVUVOIIASTRH-UHFFFAOYSA-N 2,3,3-trimethylnon-1-en-4-ol Chemical compound CC(=C)C(C(CCCCC)O)(C)C ITSVUVOIIASTRH-UHFFFAOYSA-N 0.000 description 3
- LBMVIOAWCMBBHO-UHFFFAOYSA-N 2,3,3-trimethylnonan-4-ol Chemical compound CCCCCC(O)C(C)(C)C(C)C LBMVIOAWCMBBHO-UHFFFAOYSA-N 0.000 description 3
- GTOUIROEZSWWKX-UHFFFAOYSA-N 2,3,3-trimethyloct-1-en-4-ol Chemical compound CC(=C)C(C(CCCC)O)(C)C GTOUIROEZSWWKX-UHFFFAOYSA-N 0.000 description 3
- GMPITEYGIDSFPZ-UHFFFAOYSA-N 2,4,4,5-tetramethylhex-5-en-3-one Chemical compound CC(C)C(=O)C(C)(C)C(C)=C GMPITEYGIDSFPZ-UHFFFAOYSA-N 0.000 description 3
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- JZLXEKNVCWMYHI-UHFFFAOYSA-N gingerol Natural products CCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C1 JZLXEKNVCWMYHI-UHFFFAOYSA-N 0.000 description 1
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- ZQPCOAKGRYBBMR-VIFPVBQESA-N grapefruit mercaptan Chemical compound CC1=CC[C@H](C(C)(C)S)CC1 ZQPCOAKGRYBBMR-VIFPVBQESA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- XAPCMTMQBXLDBB-UHFFFAOYSA-N hexyl butyrate Chemical compound CCCCCCOC(=O)CCC XAPCMTMQBXLDBB-UHFFFAOYSA-N 0.000 description 1
- GOKKOFHHJFGZHW-UHFFFAOYSA-N hexyl propanoate Chemical compound CCCCCCOC(=O)CC GOKKOFHHJFGZHW-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
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- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
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- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- PQCYCHFQWMNQRJ-UHFFFAOYSA-N isobutyric acid octyl ester Natural products CCCCCCCCOC(=O)C(C)C PQCYCHFQWMNQRJ-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- YJSUCBQWLKRPDL-UHFFFAOYSA-N isocyclocitral Chemical compound CC1CC(C)=CC(C)C1C=O YJSUCBQWLKRPDL-UHFFFAOYSA-N 0.000 description 1
- SZNYYWIUQFZLLT-UHFFFAOYSA-N isopropylmethyl ether Natural products CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N jasmonic acid Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
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- 150000007517 lewis acids Chemical class 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
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- BFBPISPWJZMWJN-UHFFFAOYSA-N methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N=CCC(C)CCCC(C)(C)O BFBPISPWJZMWJN-UHFFFAOYSA-N 0.000 description 1
- RBAUBIIMPLZNGC-UHFFFAOYSA-N methyl 2-[[3-(4-tert-butylphenyl)-2-methylpropylidene]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N=CC(C)CC1=CC=C(C(C)(C)C)C=C1 RBAUBIIMPLZNGC-UHFFFAOYSA-N 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
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- UPPSFGGDKACIKP-UHFFFAOYSA-N p-Tolyl isobutyrate Chemical compound CC(C)C(=O)OC1=CC=C(C)C=C1 UPPSFGGDKACIKP-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
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
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- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- QKNZNUNCDJZTCH-UHFFFAOYSA-N pentyl benzoate Chemical compound CCCCCOC(=O)C1=CC=CC=C1 QKNZNUNCDJZTCH-UHFFFAOYSA-N 0.000 description 1
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 description 1
- 235000011197 perejil Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- WFNDDSQUKATKNX-UHFFFAOYSA-N phenethyl butyrate Chemical compound CCCC(=O)OCCC1=CC=CC=C1 WFNDDSQUKATKNX-UHFFFAOYSA-N 0.000 description 1
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-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
- 229950009195 phenylpropanol Drugs 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000001631 piper nigrum l. fruit oil black Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001367 polianthes tuberosa l. flower oil Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTUCQKRAQSWLOP-UHFFFAOYSA-N propan-2-yloxymethylbenzene Chemical compound CC(C)OCC1=CC=CC=C1 NTUCQKRAQSWLOP-UHFFFAOYSA-N 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 210000000614 rib Anatomy 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- QJVXKWHHAMZTBY-KSXIZUIISA-N syringin Natural products COc1cc(C=CCO)cc(OC)c1O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O QJVXKWHHAMZTBY-KSXIZUIISA-N 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- YKFLAYDHMOASIY-UHFFFAOYSA-N terpinene-gamma Natural products CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000012749 thinning agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- HRHOWZHRCRZVCU-UHFFFAOYSA-N trans-hex-2-enyl acetate Natural products CCCC=CCOC(C)=O HRHOWZHRCRZVCU-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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
- WKJHMKQSIBMURP-UHFFFAOYSA-N tridecanenitrile Chemical compound CCCCCCCCCCCCC#N WKJHMKQSIBMURP-UHFFFAOYSA-N 0.000 description 1
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- WRFZKAGPPQGDDQ-UHFFFAOYSA-N valeryl hexanoate Chemical compound CCCCCOC(=O)CCCCC WRFZKAGPPQGDDQ-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables 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
- YEIGUXGHHKAURB-VAMGGRTRSA-N viridin Chemical compound O=C1C2=C3CCC(=O)C3=CC=C2[C@@]2(C)[C@H](O)[C@H](OC)C(=O)C3=COC1=C23 YEIGUXGHHKAURB-VAMGGRTRSA-N 0.000 description 1
- 108010086097 viridin Proteins 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
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 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
- A23L27/2026—Hydroxy compounds
-
- 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
- A23L27/84—Flavour masking or reducing agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
- C07C29/143—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 ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Seasonings (AREA)
Abstract
本发明涉及新类别的衍生自2,3‑二甲基丁烯的有气味的醇(气味剂),其可用作香味或风味物质,特别是在向香料、芳香或除臭/掩蔽组合物提供具有复杂特征的天然松嗅觉香韵方面。
Description
技术领域
本发明涉及新类别的有气味的醇,其可用作香味或风味物质,特别是在向香料、芳香或除臭/掩蔽组合物提供具有复杂气味特征的天然松嗅觉香韵方面,并且还赋予所述组合物一种或多种以下优点/性质:类似于薄荷醇的清凉效果性质,但具有更天然的印象、高扩散性和/或溶解性。本发明还涉及包含所述新类别的气味剂醇的香味、风味和/或除臭/掩蔽组合物。本发明还涉及可用于本发明的新型香味、风味和/或除臭/掩蔽组合物中的所述气味剂。本发明还涉及生产所述气味剂/化合物和相应的含有所述气味剂/化合物的香味、风味和/或除臭/掩蔽组合物的方法。
背景技术
香料工业和/或调味料工业主要利用合成分子作为原料成分。特别地,引入新型气味剂/化合物和/或包含所述气味剂/化合物的新型香味、风味和/或除臭/掩蔽组合物是合乎需要的。
对于工业应用,当各种产品可源自一种基本的骨架/原材料时,则是有益的。如果原料在某些方面是排他性的,则这将变得甚至更加有益。2,3-二甲基丁烯(1)和(2)几乎排他用于制备取代的四氢化萘(3),且特别是制备吐纳麝香(Tonalid)(4)。
因此,申请人在其研究和开发活动过程中,开始开发基于2,3-二甲基丁烯(1)和(2)作为原材料用于新型气味剂的产品。本发明的一个或多个实施方案的优点在于,所要求保护的衍生自2,3-二甲基丁烯的气味剂/化合物可赋予和/或加强特定的嗅觉香韵,特别是为香味、风味和/或除臭/掩蔽组合物提供具有复杂气味特征的天然松嗅觉香韵方面,并且还赋予所述组合物一种或多种以下优点/性质:类似于薄荷醇的清凉效果性质,但具有更天然的印象、高扩散性和/或溶解性。
Haller和Bauer的题为《Methylation of isovalerone》的文章(Comptes rendushebdomadaires des séances de l'Académie des sciences,第156卷,第1期,1913年4月28日,第1295-1298页)公开了二异丁基酮甲基化的方法。在第1297-1298页,作者描述了2,3,3,5,5,6-六甲基庚-4-酮(四甲基二异丁基酮)的合成。由于新合成的四甲基二异丁基酮不形成肟也不形成缩氨基脲(换句话说,这种化合物没有经历在可利用光谱学方法之前的时期使用的用于定性分析羰基化合物的特征反应),作者决定将假定的酮还原成醇,所述醇通过与异氰酸苯酯反应形成相应的苯基脲烷,从而证明成功地合成了所需的四甲基二异丁基酮。出于分析目的而合成的中间体醇(2,3,3,5,5,6-六甲基庚-4-醇)表现出强烈的冰片样气味。
Barbot等人的题为《Action d’organometalliques alpha-ethyleniques surles esters;applications de l’isomerisation thermique d’alcoolates zinciques ala preparation d’alcools beta,beta’-diethyleniques》的文章(Bulletin de laSociete Chimique de France,Societe Francaise de Chimie.法国巴黎,第6期,1989年1月1日,第864-871页)分别公开了通过将格氏试剂双重加成到甲酸甲酯上获得的2,3,3,5,5,6-六甲基庚-1,6-二烯-4-醇和2,3,3,6,7-五甲基辛-1,6-二烯-4-醇。
Suzuki等人的题为《Transition-Metal-Free Reductive Coupling of 1,3-Butadienes with Aldehydes Catalyzed by Dibutyliodotin Hydride》的文章(OrganicLetters,第19卷,第19期,2017年10月6日,第5392-5394页)在他们关于1,3-二烯与醛的偶合的研究的上下文中公开了2,4,4,5-四甲基己-5-烯-3-醇和2,3,3,6-四甲基庚-1-烯-4-醇,以实现不使用过渡金属催化剂的偶合反应。
Snider等人的题为《Dimethylaluminum chloride catalyzed ene reactions ofaldehydes》的文章(J.Am.Chem.Soc.,1982,104(2),第555-563页)公开了通过由二甲基氯化铝介导的脂族醛和芳族醛的烯反应获得的3,3,4-三甲基戊-4-烯-2-醇和2,3,3,6-四甲基庚-1-烯-4-醇。Smith等人公开“3-Chloro-1-lithiopropene,a FunctionalOrganolithium Reagent,and Its Reactions with Alkylboronates To Give 3-Alkylprop-1-en-3-ols”,J.Org.Chem.,2013,78(18),第9526-9531页的文章公开了4,4,5-三甲基己-1-烯-3-醇。
发明内容
本发明公开了新型香味、风味和/或除臭/掩蔽组合物,其包含选自式(7)或式(8)的化合物的醇
其中R是具有1至6个碳原子的烷基或具有2至6个碳原子的烯基,并且其中式(8)的化合物不能是2,3,3,5,5,6-六甲基庚-4-醇。
在根据本发明的一个实施方案中,R是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-甲基丙-1-烯-2-基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
在另一个实施方案中,本发明的化合物可以是手性的,例如,它们可作为立体异构混合物(更具体地作为对映体的混合物)、R异构体、S异构体、R异构体和S异构体的外消旋混合物和/或非外消旋混合物存在,并且它们也可有利地以纯形式或作为混合物使用。
在另一个实施方案中,本发明的化合物(其中R基团为烯基)可作为异构体混合物存在,更具体地作为Z异构体、E异构体和/或Z异构体和E异构体的混合物存在,并且它们也可以纯形式或作为混合物有利地使用。
具体实施方式
表征根据本发明的化合物的术语“气味剂”意味着,在人类中,其触发了一种气味感觉,这种感觉优选是令人愉快的;因此,它常规用于加香工业和卫生制品、洗涤剂、清洁剂、个人保健产品、化妆品等。为了本发明和所附权利要求书的目的,术语“气味剂”包括“芳香物质”。芳香物质是通常用来指为食品提供气味和/或风味的物质的术语。
式(7)或式(8)的醇化合物可以单独使用,以其混合物使用,或与基础材料组合使用。
如本文所用,“基础材料”包括所有已知的香味/风味材料,其选自广泛范围的天然产品,如:精油、提取物、树脂型物(resinoid)或分离物和合成材料,例如:烃、醇、醛和酮、醚和缩醛、酯和内酯、腈、肟或杂环,和/或与一种或多种常规与气味剂联合用于香味和/或风味组合物中的成分或赋形剂/佐剂(例如:溶剂/稀释剂、稳定剂、载体材料和本领域常用的其他助剂)混合。
根据式(7)或式(8)的醇化合物可用于广泛范围的香味应用,例如在任何精细和功能性香料的领域内,例如香料、空气护理产品、家居产品、洗衣产品、身体护理产品和化妆品。所述化合物可以根据具体应用以及其他气味剂成分的性质和量,以广泛不同的量使用。
根据本发明的一个优选的实施方案,根据本发明的香味、风味和/或除臭/掩蔽组合物含有至少一种如前所述的根据式(7)或式(8)的醇化合物,其量在每种情况下相对于整个组合物为0.00001重量%和99.9重量%之间,例如在0.0001重量%和95重量%之间,例如在0.001重量%和25重量%之间,优选在0.01重量%和15重量%之间,更有利地在0.1重量%和10重量%之间,特别是在1重量%和5重量%之间。
根据本发明的一个特别优选的实施方案,除了根据本发明的式(7)或式(8)的化合物之外,根据本发明的香味、风味和/或除臭/掩蔽组合物还包含另外的气味剂,例如相对于整个香味和/或风味组合物,其量为0.1重量%至99.9重量%,优选5-90重量%,特别是15-70重量%。
如上文所述的式(7)或式(8)的化合物可简单地通过将至少一种式(7)或式(8)的化合物或包含所述式(7)或式(8)的化合物的香味组合物与消费品基料直接混合而用于消费品基料中;或者在较早的步骤中,它们可以用捕集材料捕集,所述捕集材料为例如聚合物、胶囊、微胶囊和/或纳米胶囊、脂质体、成膜剂、吸收剂(如活性炭或沸石)、环状低聚糖、环状甘脲以及其中两种或更多种的混合物;或者它们可以化学键合到基质上,所述基质适应于在施加外部刺激(如光、酶、空气、水等)时释放该香味分子,然后与消费品基料混合。
因此,本发明可用于制造香味、风味和/或除臭/掩蔽组合物的现有方法,所述方法包括使用常规技术和方法,通过将式(7)或式(8)的化合物直接混合到消费品基料中,或者通过混合包含所述式(7)或式(8)的化合物的香味、风味和/或除臭/掩蔽组合物,然后可将其与消费品基料混合,来并入式(7)或式(8)的化合物作为香味、风味和/或除臭/掩蔽成分。通过添加嗅觉可接受量的至少一种如上文所述的本发明的式(7)或式(8)的化合物,可改善、增强和/或改变消费品基料的气味香韵。
本发明提供了包含选自式(7)或式(8)的化合物的醇的香味、风味和/或除臭/掩蔽组合物
其中R是具有1至6个碳原子的烷基或具有2至6个碳原子的烯基,并且其中式(8)的化合物不能是2,3,3,5,5,6-六甲基庚-4-醇。
在根据本发明的一个实施方案中,R是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-甲基丙-1-烯-2-基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
在根据本发明的一个实施方案中
-对于式(7)的化合物,R不能是甲基、异丙基或异丁基,并且
-对于式(8)的化合物,R不能是甲基、异丙基或乙烯基。
在根据本发明的一个实施方案中,R不能是甲基、异丙基、异丁基或乙烯基。
在根据本发明的一个实施方案中,式7的化合物不能是2,3,3,5,5,6-六甲基庚-1,6-二烯-4-醇或2,3,3,6,7-五甲基辛-1,6-二烯-4-醇。
在根据本发明的一个实施方案中,香味、风味和/或除臭/掩蔽组合物包含式(7)或式(8)的化合物,其选自下表中命名或绘制的任何化合物
和/或两种或更多种所述化合物的混合物。
申请人还发现,从嗅觉角度来看,式(7)或式(8)的化合物具有使其本身直接用于草本、芬芳和柑桔组合物而没有“合成”效果的明显天然的松特性。式(7)或式(8)的化合物为组合物提供了闪耀的清新感,并表现出与薄荷醇类似的清凉效果性质,但具有更天然的印象。
例如,当化合物(7)中的R被选择为乙基时,申请人发现从嗅觉(olactory)的角度来看,所述化合物具有明显的天然品质,使人想起冷杉针叶和薄荷油的组合,以及清凉的感觉。此外,与其他气味剂如冰片相比,这种化合物具有更大的扩散性,甚至进一步增加了天然效果。
醇
在一个实施方案中,本发明还提供了可用于本发明的香料、芳香和/或除臭/掩蔽组合物中的式(7)的新化合物
其中R是具有2至6个碳原子的烷基,或具有2至6个碳的烯基,条件是
-R不能是异丙基或异丁基,并且
-式7化合物不能是2,3,3,5,5,6-六甲基庚-1,6-二烯-4-醇或2,3,3,6,7-五甲基辛-1,6-二烯-4-醇。
在适用于式(7)的化合物的根据本发明的一个实施方案中,R是乙基、正丙基、正丁基、仲丁基、叔丁基、2-甲基丙-1-烯-2-基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
在适用于式(7)的化合物的另一个实施方案中,R是具有2至6个碳原子的直链烷基或具有2至6个碳的烯基。
在一个实施方案中,本发明还提供了可用于本发明的香料、芳香和/或除臭/掩蔽组合物中的式(8)的新化合物
其中R是具有2至6个碳原子的烷基,或具有3至6个碳的烯基,条件是R不能是异丙基,并且式(8)的化合物不能是2,3,3,5,5,6-六甲基庚-4-醇。
在适用于式(8)的化合物的根据本发明的一个实施方案中,R是乙基、正丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
在适用于式(8)的化合物的另一个实施方案中,R是具有2至6个碳原子的直链烷基,或具有3至6个碳的烯基。
在根据本发明的一个实施方案中,可用于本发明的香料、芳香和/或除臭/掩蔽组合物中的式(7)和/或式(8)的新化合物选自下表中命名或绘制的任何化合物
和/或两种或更多种所述化合物的混合物。
制备
在根据本发明的一个优选的实施方案中,式(7)和/或式(8)的化合物可有利地由2,3-二甲基丁烯经由如下所示的酰化、任选的氢化和羰基还原反应程序制备。
其中R是具有1至6个碳原子的烷基或具有2至6个碳原子的烯基。
在根据本发明的一个优选的实施方案中,式(7)和/或式(8)的化合物可有利地由2,3-二甲基丁-1-烯经由如下所述的酰化、任选的氢化和羰基还原反应程序制备。
在一个实施方案中,式(7)的三甲基烯醇和式(8)的三甲基烷醇可有利地分别由相应的酮5或6通过还原式(5)或式(6)的化合物的羰基来制备。可以使用任何适当的羰基还原方法。在根据本发明的一个实施方案中,有利地使用在乙醇和水的混合物中的硼氢化钠。
在另一个实施方案中,式(8)的三甲基烷醇可有利地由相应的酮5通过直接还原式5化合物的羰基和双键两者来制备。可以使用任何适当的还原方法。在根据本发明的一个实施方案中,可以有利地使用在Pt/C存在下的氢。
下表示出了由通式5或6表示的所述相应酮(在本说明书和所附权利要求书中称为“母体”酮)。
2,3-二甲基丁烯
根据本发明的2,3-二甲基丁烯化合物可以选自2,3-二甲基-1-丁烯、2,3-二甲基-2-丁烯或其混合物;优选2,3-二甲基-2-丁烯或2,3-二甲基-2-丁烯与2,3-二甲基-1-丁烯的混合物。
任选的异构化步骤
在根据本发明的一个实施方案中,优选执行异构化步骤以将2,3-二甲基-1-丁烯转化为2,3-二甲基-2-丁烯。这个异构化步骤优选例如在起始材料为2,3-二甲基-1-丁烯时或起始材料为2,3-二甲基-2-丁烯与2,3-二甲基-1-丁烯的混合物且2,3-二甲基-1-丁烯的含量大于2,3-二甲基-2-丁烯的含量时执行。可以使用任何适当的烯烃异构化方法;作为说明性和非限制性的实例,可以有利地使用碱催化和/或酸催化的异构化方法。在根据本发明的一个实施方案中,有利地使用离子交换树脂酸催化剂,例如酸形式的大孔树脂(Amberlyst)催化剂。
酰化合成步骤
因此,在本发明的一个实施方案中,使2,3-二甲基丁烯进行酰化合成步骤,以形成可以由下式表示的式(5)的酮
其中R是具有1至6个碳原子的烷基或具有2至6个碳原子的烯基。
在本发明的一个实施方案中,通过使2,3-二甲基丁烯与酸酐或酰氯反应,优选随后进行常规后处理(例如水洗、除去未反应的反应物和/或溶剂和蒸馏)来获得产物。
在根据本发明的一个实施方案中,R是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-甲基丙-1-烯-2-基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
可以使用产生上述式(5)的酮化合物的任何适当的酰化方法;作为说明性和非限制性的实例,酰化在2,3-二甲基丁烯和羧酸酐(例如乙酸酐或丙酸酐)的存在下执行。这个工艺步骤可以有利地在酸催化剂的存在下进行。
这个工艺步骤可以有利地在路易斯或布朗斯特酸催化剂(例如氯化锌、甲磺酸、三氟甲磺酸等)存在下操作。这个工艺步骤可以有利地在无溶剂的情况下或使用合适的非质子极性溶剂(例如二氯甲烷)操作。
在根据本发明的一个实施方案中,酰化步骤之后优选是烷基化步骤;例如,使2,3-二甲基丁烯进行酰化合成步骤,以形成低级烷基酮化合物,然后将其转化为所需的高级烷基酮。在根据本发明的一个实施方案中,酰化步骤之后优选是烷基化步骤;例如,使2,3-二甲基丁烯进行酰化合成步骤,以形成如由下式(5a,即其中R=CH3)表示的式(5a)的化合物
然后将其转化为如由下式表示的式(5b)的化合物
其中R1选自具有1至5个碳原子的烷基、仅含一个碳-碳双键且具有至多5个碳原子的烯基或具有至多5个碳原子的氧代-烷基。
可以通过使2,3-二甲基丁烯进行酰化合成步骤直接形成式(5b)的化合物或通过使式(5a)的化合物进行烷基化步骤而获得的式(5b)的化合物可以进一步烷基化以形成式(5c)的化合物。
其中R1选自具有1至4个碳原子的烷基、仅含一个碳-碳双键且具有至多4个碳原子的烯基、具有至多4个碳原子的氧代-烷基,且R2选自具有1至4个碳原子的烷基、仅含一个碳-碳双键且具有至多4个碳原子的烯基、具有至多4个碳原子的氧代-烷基,并且基团R1和R2中存在的碳原子总数不大于5。
可以通过使2,3-二甲基丁烯进行酰化合成步骤以直接形成式(5c)的化合物,或通过使式(5b)的化合物进行烷基化步骤,或通过使化合物(5a)进行双烷基化步骤而获得的式(5c)的化合物可以进一步烷基化以形成式(5d)的化合物。
其中R1为具有1至3个碳原子的烷基、仅包含一个碳-碳双键且具有至多3个碳原子的烯基、具有至多3个碳原子的氧代-烷基,且R2选自具有1至3个碳原子的烷基、仅包含一个碳-碳双键且具有至多3个碳原子的烯基、或具有至多3个碳原子的氧代-烷基,R3选自具有1至3个碳原子的烷基、仅包含一个碳-碳双键且具有至多3个碳原子的烯基、或具有至多3个碳原子的氧代-烷基,并且基团R1、R2和R2中存在的碳原子总数不大于5。
当式(5c)和(5d)的化合物中R1、R2或R3基团中的至少两个相同时,这些相同基团的引入可以在单个烷基化步骤中执行。
当2,3-二甲基-2-丁烯是起始材料时,本发明的合成方法的酰化步骤的优点是其可以耐受2,3-二甲基-1-丁烯的存在。因此,虽然本发明优选使用纯2,3-二甲基-2-丁烯用于酰化步骤,但是其也可以有利地耐受低于99%,例如低于95%的2,3-二甲基-2-丁烯与2,3-二甲基-1-丁烯的起始材料摩尔比;所述摩尔比优选高于50%,例如高于75%,或甚至高于85%。
在根据本发明的另一个实施方案中,酰化步骤优选从纯2,3-二甲基丁-1-烯开始执行。
在根据本发明的一个供选实施方案中,酰化步骤之后优选是醇醛缩合步骤;例如,使2,3-二甲基丁烯进行酰化合成步骤,以形成如由下式(5a,即其中R=CH3)表示的式(5a)的化合物
然后将其转化为如由下式表示的式(5e)的化合物
其中R1选自氢、具有1至4个碳原子的烷基、具有至多5个碳原子的氧代-烷基,且R2选自氢、具有1至4个碳原子的烷基、具有至多4个碳原子的氧代-烷基,并且基团R1和R2中存在的碳原子总数不大于4。
在本发明的一个实施方案中,可以通过使2,3-二甲基丁烯进行酰化合成步骤以直接形成式(5b)的化合物或通过使式(5a)的化合物进行烷基化步骤而获得的式(5b)的化合物可以进行醇醛缩合步骤以形成式(5f)的化合物。
其中R1选自氢、具有1至4个碳原子的烷基、具有至多4个碳原子的氧代-烷基,且R2选自氢、具有1至4个碳原子的烷基、具有至多4个碳原子的氧代-烷基,且R3选自氢、具有1至4个碳原子的烷基、具有至多4个碳原子的氧代-烷基,并且基团R1和R2和R3中存在的碳原子总数不大于4。
在根据本发明的一个实施方案中,酰化步骤之后优选是氢化步骤和任选的烷基化步骤;例如,使2,3-二甲基丁烯进行酰化合成步骤,然后进行氢化合成步骤,以形成根据本发明的式(6)的饱和酮。
在根据本发明的一个实施方案中,酰化步骤之后优选是氢化步骤和烷基化步骤;例如,使2,3-二甲基丁烯进行酰化合成步骤,然后进行氢化合成步骤,以形成如由下式(6a,即其中R=CH3)表示的式(6a)的化合物
然后将其转化为如由下式表示的式(6b)的化合物
其中R1选自具有1至5个碳原子的烷基、仅含一个碳-碳双键且具有至多5个碳原子的烯基或具有至多5个碳原子的氧代-烷基。
在本发明的一个实施方案中,可以通过使2,3-二甲基丁烯进行酰化合成步骤以直接形成式(5b)的化合物或通过使式(6a)的化合物进行烷基化步骤而获得的式(5b)的化合物可以进一步烷基化以形成式(6c)的化合物。
其中R1选自具有1至4个碳原子的烷基、仅含一个碳-碳双键且具有至多4个碳原子的烯基、具有至多4个碳原子的氧代-烷基,且R2选自具有1至4个碳原子的烷基、仅含一个碳-碳双键且具有至多4个碳原子的烯基、具有至多4个碳原子的氧代-烷基,并且基团R1和R2中存在的碳原子总数不大于5。
在本发明的一个实施方案中,可以通过使2,3-二甲基丁烯进行酰化合成步骤以直接形成式(6c)的化合物或通过使式(6b)的化合物进行烷基化步骤或通过使化合物(6a)进行双烷基化步骤而获得的式(6c)的化合物可以进一步烷基化以形成式(6d)的化合物。
其中R1为具有1至3个碳原子的烷基、仅包含一个碳-碳双键且具有至多3个碳原子的烯基、或具有至多3个碳原子的氧代-烷基,且R2选自具有1至3个碳原子的烷基、仅包含一个碳-碳双键且具有至多3个碳原子的烯基、或具有至多3个碳原子的氧代-烷基,R3选自具有1至3个碳原子的烷基、仅包含一个碳-碳双键且具有至多3个碳原子的烯基、或具有至多3个碳原子的氧代-烷基,并且基团R1、R2和R2中存在的碳原子总数不超过5。
当式(6c)和(6d)的化合物中R1、R2或R3基团中的至少两个相同时,这些相同基团的引入可以在单个烷基化步骤中执行。
在根据本发明的一个实施方案中,酰化步骤之后是氢化步骤,优选之后是醇醛缩合步骤;例如,使2,3-二甲基丁烯进行酰化合成步骤,然后进行氢化步骤,以形成如由下式(6a,即其中R=CH3)表示的式(6a)的化合物
然后将其转化为如由下式表示的式(6e)的化合物
其中R1选自氢、具有1至4个碳原子的烷基或具有至多4个碳原子的氧代-烷基,且R2选自氢、具有1至4个碳原子的烷基或具有至多4个碳原子的氧代-烷基,并且基团R1和R2中存在的碳原子总数不大于4。
在根据本发明的一个实施方案中,可以通过使2,3-二甲基丁烯进行酰化合成步骤以直接形成式(6b)的化合物或通过使式(6a)的化合物进行烷基化步骤而获得的式(6b)的化合物可以进行醇醛缩合步骤以形成式(6f)的化合物。
其中R1选自氢、具有1至4个碳原子的烷基或具有至多4个碳原子的氧代-烷基,且R2选自氢、具有1至4个碳原子的烷基或具有至多4个碳原子的氧代-烷基,且R3选自氢、具有1至4个碳原子的烷基或具有至多4个碳原子的氧代-烷基,并且基团R1和R2和R3中存在的碳原子总数不大于4。
因此,酮(5)和(6)的合成可以有利地根据以下图式实现:
可以使用分别产生式(5b-d)和(6b-d)的化合物的任何适当的烷基化方法;作为说明性和非限制性的实例,烷基化在具有通用结构(5)或(6)的2,3-二甲基丁烯和烷基卤或硫酸烷基酯(甲基碘、硫酸二甲酯等)的酰化产物存在下在碱(氢氧化钾、叔丁醇钾等)存在下执行。
可以使用分别产生式(5e-f)和(6e-f)的化合物的任何适当的醇醛缩合方法;作为说明性和非限制性的实例,醇醛缩合在具有通用结构(5)或(6)的2,3-二甲基丁烯和醛或酮的酰化产物存在下在碱(氢氧化钾、叔丁醇钾等)或酸(盐酸、硫酸等)存在下进行。
因此,饱和酮的合成可以有利地根据以下图式实现:
在根据本发明的一个实施方案中,式(7)的化合物可以有利地通过以下连续步骤制备:
·使2,3-二甲基丁烯进行酰化合成步骤,任选地随后进行烷基化步骤,以形成不饱和酮化合物(5),和
·使所述不饱和酮化合物进行还原步骤以形成式(7)的醇化合物。
在根据本发明的一个实施方案中,式(8)的化合物可以有利地通过以下连续步骤制备:
·使2,3-二甲基丁烯进行酰化合成步骤,任选地随后进行烷基化步骤,以形成不饱和酮化合物(5),和
·使不饱和酮化合物(5)进行氢化步骤以形成饱和酮化合物(6)
然后使其进行还原步骤以形成式(8)的醇化合物。
本发明的合成方法的羰基还原步骤的优点在于,其可以耐受先前合成步骤的反应物的存在,即如上文所述的来自酰化步骤和/或来自组合的酰化/烷基化或来自组合的酰化/醇醛缩合步骤的反应物。
因此,在本发明的一个实施方案中,酰化步骤可以在如下情况下有利地执行:
-2,3-二甲基-2-丁烯与中间体酮的摩尔比高于0,例如高于0.05;和/或
-来自酰化的羧酸酐或路易斯酸(如三氯化铝和/或氯化锌)与中间体酮的摩尔比高于0,例如高于0.05;和/或
-来自酰化步骤的催化剂残余物与中间体酮的摩尔比高于0,例如高于0.05。
在本发明的一个实施方案中,羰基还原步骤也可以在如下情况下有利地执行:
-2,3-二甲基-2-丁烯与中间体酮的摩尔比低于0.2,例如低于0.15;和/或
-来自酰化步骤的羧酸酐与中间体酮的摩尔比低于0.2,例如低于0.15;和/或
-来自酰化步骤的催化剂残余物与中间体酮的摩尔比低于0.2,例如低于0.15。
在本发明的一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物有利地用作香料组合物。根据本发明的香料组合物通常包括香水、古龙水、淡香水和/或浓香水。在本发明的一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物有利地用于化妆品制剂、个人护理产品、清洁产品、织物柔软剂和/或空气清新剂等。此外,在本发明实施方案的范围内,本文所述的新型香味、风味和/或除臭/掩蔽组合物和/或式(7)或式(8)的新型化合物可以整合到建筑材料、墙壁和地板覆盖物、车辆组件等中。
通常,除了本文所述的新型气味剂和/或香味、风味和/或除臭/掩蔽组合物之外,合适的香味、风味或除臭组合物可以有利地包含常规成分,例如溶剂、载体、稳定剂、乳化剂、增湿剂、分散剂、稀释剂、增稠剂、冲淡剂、其他气味剂和/或佐剂等。
式(7)和/或(8)的化合物与许多已知的天然或合成香味、风味和/或除臭/掩蔽材料组合,其中天然成分的范围不仅可以包括易挥发的而且可以包括半挥发性和轻微挥发性的组分,并且合成成分的范围可以包括来自许多物质类别的代表,如从以下非限制性的汇编中将显而易见的:
天然产物,例如:
香旱芹油(Ajowan oil)、香树油(Amyris oil)、蒿草油(Armoise oil)、艾草油(Artemisia oil)、罗勒油(Basil oil)、纯净蜂蜡(Bees wax absolute)、佛手柑油(Bergamot oil)、桦木焦油(Birch tar oil)、黑胡椒油(Black pepper oil)、黑胡椒油树脂(Black pepper oleoresin)、樟脑油(Camphor oil)、依兰油(Cananga oil)、藏茴香油(Caraway oil)、小豆蔻油(Cardamom oil)、胡萝卜籽油、纯净海狸香(Castoreumabsolute)、雪松叶油(Cedar leaf oil)、雪松木油(Cedarwood oil)、芹菜籽油(Celeryseed oil)、春黄菊油(Chamomile oil)、桂皮油(Cinnamon bark oil)、桂叶油、纯净岩蔷薇油(Cistus absolute)、岩蔷薇油(Cistus oil)、香茅油(Citronella oil)、香茅萜(Citronella terpenes)、鼠尾草油(Clary sage oil)、精馏丁香油(Cloveoilrectified)、康酿克油(Cognac oil white)、芫荽籽油(Coriander seed oil)、孜然籽油(Cumin seed oil)、柏树油(Cypress oil)、印蒿油(Davana oil)、莳萝籽油(Dillseedoil)、榄香脂油(Elemi oil)、榄香树脂型物(Elemi resinoid)、桉树油(Eucalyptusoil)、冷杉叶油(Fir needle oil)、白松香油(Galbanum oil)、天竺葵油(Geranium oil)、印度姜油(Ginger oil Indian)、葡萄柚油(Grapefruit oil)、愈创木油(Guaiacwoodoil)、古芸香胶(Gurjun balsam)、纯净茉莉油(Jasmin absolute)、甘松油(Jatamansioil)、杜松籽油(Juniper berry oil)、杜松叶油、卡胡尔油(Kachur oil)、纯净劳丹脂(Labdanumabsolute)、劳丹树脂型物(Labdanum resinoid)、熏衣草油(Lavender oil)、柠檬油、柠檬油萜、柠檬香茅草油(Lemongrass oil)、酸橙油(Lime oil)、山苍子油(Litseacubebaoil)、山苍子萜(Litsea cubeba terpenes)、Lobhan choya树脂型物、橘油(Mandarinoil)、薄荷油(Mentha arvenis oil)、柠檬薄荷油(Mentha citrata oil)、纯净含羞草油(Mimosa absolute)、没药树脂型物(Myrrh resinoid)、莎草油(Nagarmothaoil)、肉豆蔻油(Nutmeg oil)、纯净橡苔(Oakmoss absolute)、橡苔树脂型物(Oakmossresinoid)、乳香油(Olibanum oil)、乳香树脂型物(Olibanum resinoid)、橙油、牛至油(Origanum oil)、玫瑰草油(Palma rosa oil)、广藿香油(Patchouli oil)、胡椒薄荷油(Peppermint oil)、秘鲁香脂树脂型物(Peru Balsam resinoid)、卑柠油(Petitgrainoil)、松叶油(Pineneedle oil)、粉椒油(Pink pepper oil)、纯净玫瑰油(Rose absolut)、玫瑰油(Roseoil)、迷迭香油、檀香木油(Sandalwood oil)、纯净海藻油(Seaweedabsolute)、留兰香油(Spearmint oil)、印度苏刚达精油(Sugandh kokila oil)、印度苏刚达香薰油(Sugandhmantri oil)、万寿菊油(Tagete oil)、妥卢香脂树脂型物(Tolu Balsamresinoid)、纯净晚香玉油(Tuberose absolute)、姜黄油(Turmeric oil)、松节油(Turpentine oil)、缬草油(Valerian oil)、香根油(Vetiver oil)、香根萜(Vetiverterpenes)。
合成原料,例如:
酯,例如:C16醛、格蓬酯、己酸烯丙基酯、环己基丙酸烯丙基酯、庚酸烯丙基酯、苯氧基乙酸烯丙基酯、乙酸异戊酯、苯甲酸戊酯、丁酸戊酯、己酸戊酯、肉桂酸戊酯、异戊酸戊酯、苯基乙酸戊酯、丙酸戊酯、水杨酸异戊酯、乙酰化香树油(Amyris acetate)、乙酸茴香酯、乙酸苄酯、苯甲酸苄酯、丁酸苄酯、肉桂酸苄酯、甲酸苄酯、异丁酸苄酯、苄基异丁香酚、丙酸苄酯、水杨酸苄酯、惕各酸苄酯、乙酸丁酯、丁酸丁酯、丁酰乳酸丁酯、乙酸石竹烯酯(Caryophyllene acetate)、乙酸柏木酯(Cedryl acetate)、乙酸肉桂酯、丁酸肉桂酯、顺式-3-己烯基乙酸酯、顺式-3-己烯基苯甲酸酯、顺式-3-己烯基己酸酯、顺式-3-己烯基甲酸酯、顺式-3-己烯基异丁酸酯、顺式-3-己烯基-2-甲基丁酸酯、顺式-3-己烯基丙酸酯、顺式-3-己烯基水杨酸酯、顺式-3-己烯基惕各酸酯、乙酸香茅酯(Citronellyl acetate)、丁酸香茅酯、甲酸香茅酯、异丁酸香茅酯、丙酸香茅酯、惕各酸香茅酯、异丁酸三环癸烯酯(Cyclabute)、环格蓬酯(Cyclogalbanate)、环己基乙酸乙酯、乙酸癸酯、邻苯二甲酸二丁酯、丙二酸二乙酯、邻苯二甲酸二乙酯、乙酸二氢月桂烯酯(Dihydromyrcenyl acetate)、乙酸二甲基辛酯、乙酸二甲基苯基乙基原酯(Dimethyl phenyl ethyl carbinyl acetate)、己二酸二辛酯、邻苯二甲酸二辛酯、乙酸二甲基苄基原酯、丁酸二甲基苄基原酯、乙酸乙基芳樟酯(Ethyl linalyl acetate)、2-甲基丁酸乙酯、3-苯基丙酸乙酯、乙酸乙酯、乙酰乙酸乙酯、苯甲酸乙酯、丁酸乙酯、癸酸C10乙酯、己酸C6乙酯、辛酸C8乙酯、肉桂酸乙酯、庚酸乙酯、乙基己基乙酸酯、异丁酸乙酯、月桂酸乙酯、壬酸乙酯(Ethyl pelargonate)、苯氧基乙酸乙酯、乙基苯基乙酸酯、乙基苯基环氧乙烷甲酸酯(Ethyl phenyl glycidate)、丙酸乙酯、藏红花酸乙酯(Ethyl safranate)、水杨酸乙酯、戊酸乙酯、乙酸丁香酚酯(Eugenylacetate)、Evernyl、乙酸小茴香酯(Fenchyl acetate)、Floramat、Frescolat ML、乙酸乙基甲基二茂烷酯(Fructone)、三环癸烷羧酸乙酯(Fruitate)、乙酸香叶酯(Geranylacetate)、丁酸香叶酯、甲酸香叶酯、丙酸香叶酯、惕各酸香叶酯、2-乙基-6,6-二甲基-2-环己烯-1-甲酸乙酯(Givescone)、乙酸愈创木醇酯(Guaiol acetate)、二氢茉莉酮酸酯(Hedionate)、二氢茉莉酮酸甲酯(Hedione)、海菲麝香(Helvetolide)、香菠酯(Herbanate)、乙酸己酯、苯甲酸己酯、丁酸正己酯、己酸己酯、异丁酸己酯、丙酸己酯、水杨酸己酯、乙酸异冰片酯、乙酸异丁酯、异丁基苯基乙酸酯、水杨酸异丁酯、乙酸异丁香酚酯(Isoeugenyl acetate)、乙酸异壬酯、异戊酸酯、2-甲基丁酸异丙酯、肉豆蔻酸异丙酯、茉莉酯(Jasmonyl)、顺式-3-己烯醇碳酸甲酯(Liffarome)、乙酸芳樟酯(Linalyl acetate)、藿檀酯(Mahagonate)、母菊酯(Manzanate)、二氢松香醇乙酸酯(Menthanyl acetate)、乙酸薄荷酯、苯甲酸甲酯、2-甲基丁基乙酸酯、2-甲基戊丁酯(Methyl camomille)、肉桂酸甲酯、环香叶酸甲酯(Methyl cyclogeranate)、庚炔羧酸甲酯(Methyl heptine carbonate)、月桂酸甲酯、辛炔羧酸甲酯(Methyl octine carbonate)、苯基乙酸甲酯、水杨酸甲酯、甲基-2-甲基丁酸酯、新福力酯(Neofolione)、乙酸诺吡酯(Nopyl acetate)、乙酸辛烯基酯、乙酸辛酯、异丁酸辛酯、乙酸对甲酚酯(Para cresyl acetate)、异丁酸对甲酚酯、苯基乙酸对甲酚酯、梨酯、2-甲基戊酸2-甲基戊酯(Peranat)、异丁酸苯氧基乙酯、乙酸苯基乙酯、丁酸苯基乙酯、甲酸苯基乙酯、异丁酸苯基乙酯、苯基乙酸苯基乙酯、丙酸苯基乙酯、水杨酸苯基乙酯、惕各酸苯基乙酯、异丁酸苯基丙酯、乙酸异戊二烯酯(Prenyl acetate)、罗曼麝香(Romandolide)、Sagecete、乙酸苏合香酯(Styrallyl acetate)、丙酸苏合香酯(Styrallylpropionate)、红桔酯(Tangerinol)、乙酸松油酯(Terpinyl acetate)、Thesaron、反式-2-己烯基乙酸酯、Tropicate、2-叔丁基环己基乙酸酯(Verdox)、乙酸三环癸烯酯(Verdylacetate)、丙酸三环癸烯酯、乙酸对叔丁基环已酯(Vertenex)、二甲基-3-苯丁醇乙酸酯(Vetikol acetate)、乙酸香根酯(Vetiveryl acetate)、Yasmolys。
内酯类,例如:黄葵内酯(Ambrettolide)、Arova N、3-丙亚基-1-异苯并呋喃酮(Celeriax)、δ-癸内酯、γ-癸内酯、δ-十二内酯、γ-十二内酯、巴西酸亚乙酯(Ethylenebrassylate)、环十五内酯(Exaltolide)、γ-庚内酯、δ-己内酯、γ-己内酯、甲基莱托酮(Methyl laitone)、甲基辛内酯、δ-壬内酯、γ-壬内酯、八氢香豆素、δ-辛内酯、γ-辛内酯、Rootylone、环十六内酯(Silvanone supra)、δ-十一内酯、γ-十一内酯、γ-戊内酯、10-氧杂十六内酯(OHD麝香)、香豆素(Coumarin)、环十五烯内酯(Habanolide)、茉莉内酯(Jasmolactone)。
醛类,例如:乙醛、阿道克醛(Adoxal)、C10醛、异C11醛(Aldehyde C11 iso)、C11moa醛、十一碳烯醛C11(Aldehyde C11 undecylenic)、十一碳醛C11(AldehydeC11undecylic)、月桂醛C12、醛C12 MNA、茴香醛(Anisaldehyde)、戊基肉桂醛、苯甲醛、波洁红醛(Bourgeonal)、樟脑烯醛(Campholenaldehyde)、Cantonal、紫罗兰醛(Cetonal)、肉桂醛、顺式-4-癸烯醛、顺式-6-壬烯醛、柠檬醛、香茅醛、香茅基氧基乙醛(Citronellyloxyacetaldehyde)、可卡醛(Cocal)、枯茗醛(Cuminaldehyde)、Curgix、Cyclal C、兔耳草醛(Cyclamen aldehyde)、铃兰甲醛(Cyclomyral)、女贞醛(Cyclovertal)、癸烯醛9、Dupical、柑青醛(Empetal)、乙基香草醛(Ethyl vanillin)、海风醛(Floralozone)、花青醛(Florhydral)、癸二烯醛(Geraldehyde)、胡椒基丙醛(Helional)、洋茉莉醛(Heliotropin)、庚醛、己醛、己基肉桂醛、新铃兰醛(Hivernal neo)、氢化阿托醛(Hydratropaldehyde)、羟基香茅醛、内十一烯醛(Intreleven aldehyde)、异丁酸香兰酯(Isobutavan)、异环柠檬醛(Isocyclocitral)、异戊醛、铃兰醛(Lilial)、新柠檬醛(Limonenal)、马赛醛(Maceal)、梅弗兰醛(Mefranal)、甜瓜醛(Melonal)、甲基肉桂醛、反式-2-顺式-6-壬二烯醛、壬醛、辛醛、Oncidal、对甲苯醛(Para tolyl aldehyde)、苯基乙醛、苯基丙醛、甲基柑青醛B(Precyclemone B)、藏红花醛(Safranal)、水杨醛、清风醛(Scentenal)、丁香醛(Syringa aldehyde)、反式-4-癸烯醛、反式-2-十二烯醛、反式-2-己烯醛、反式-2-壬醛、新女贞醛(Trifernal)、香草醛、藜芦醛(Veratraldehyde)、鲜草醛(Vernaldehyde)。
酮类,例如:山楂花酮(Acetanisol)、乙偶姻(Acetoin)、苯乙酮、Aldron、烯丙基紫罗兰酮(Allyl ionone)、苯甲酮、苄基丙酮、西瓜酮(Calone)、莰酮(Camphor)、d-香芹酮、l-香芹酮、喀什米尔木麝香(Cashmeran)、柏木基甲基酮(Cedryl methyl ketone)、二氢茉莉酮酸甲酯(Cepionate)、Claritone、Cosmone、萨利麝香(Crysolide)、Cyclotene、大马烯酮(Damascenone)、大马酮α、大马酮β、大马酮δ、大马酮γ、二乙酰(Diacetyl)、二氢-β-紫罗兰酮、二氢茉莉酮酸酯(Dihydro isojasmonate)、二甲基辛烯酮、王朝酮(Dynascone)、乙基戊基酮、乙基麦芽酚、葑酮(Fenchone)、榛子酮(Filbertone)、香叶基丙酮(Geranylacetone)、环十六烯酮(Globanone)、庚基环戊酮、α-紫罗兰酮(Iononeα)、β-紫罗兰酮、紫罗兰酮纯(Ionone pure)、鸢尾木(Iriswood)、α-鸢尾酮(Ironeα)、龙涎酮(Iso E Super)、异葑酮(Isofenchone)、异茉莉酮T(Isojasmone T)、异洛酮K(Isolone K)、异薄荷酮(Isomenthone)、异佛尔酮、顺式-茉莉酮(Jasmone cis-)、Kambernoir、加菲力士(Kephalis)、6-五甲基庚-3-烯-2-酮(Koavone)、Lavendinal、麦芽酚(Maltol)、薄荷酮、甲基苯乙酮、甲基戊基酮、甲基庚烯酮、甲基己基酮、γ-甲基紫罗兰酮、甲基萘基酮β、甲基壬基酮、麝香烯酮(Muscenone)、麝香酮(Muscone)、桃酮(Nectaryl)、Orinox、OTBC酮、对叔丁基环己酮、Patchwood、粉檀麝香(Phantolid)、Pharaone、胡椒酮(Piperitone)、普利卡酮(Plicatone)、覆盆子酮(Raspberry ketone)、覆盆子酮甲基醚、藏花茚(Safraleine)、螺环格蓬酮纯(Spirogalbanone pure)、吐纳麝香(Tonalid)、三甲基琥珀酮(Trimofix O)、凡路酮(Veloutone)、Vetikon。
醇类,例如:羰基合成C13醇(Alcohol oxo C13)、琥珀核(Amber core)、Ambermax、龙涎香八氢萘醇(Ambrinol)、戊基乙烯基原醇(Amyl vinyl carbinol)、茴香醇(Anisicalcohol)、白檀醇(Bacdanol)、苄醇、丁醇、结晶柏木醇(Cedrol crystals)、肉桂醇、香茅醇、花冠醇(Coranol)、癸醇(Decanol)、二甲基苄基原醇、二甲基辛醇、二甲基苯基乙基原醇、二甲基庚醇(Dimetol)、葑醇(Fenchol)、己醇、异冰片(Isoborneol)、异冰片基环己醇、爪哇檀香(Javanol)、Keflorol、四甲基-4-亚甲基-2-庚醇(Kohinool)、月桂醇、Lilyflore、氧化芳樟醇(Linalool oxide)、五月铃兰醇(Mayol)、薄荷醇、赛木香醇(Norlimbanol)、辛醇、沙针醇(Osyrol)、对叔丁基环己醇、苯基异己醇(Phenoxanol)、苯氧基乙醇、苯基乙醇、苯基丙醇、丙二醇、甲基苯戊醇(Rosaphen)、玫瑰二醇、苏合香醇(Styrallyl alcohol)、三环癸烷二甲醇、四氢芳樟醇、四氢月桂烯醇、特木倍醇(Timberol)、甲基癸烯醇(Undecavertol)、顺式-3-己烯醇、左旋香茅醇(Citronellollaevo)、环花醇(Cyclofloranol)、二氢芳樟醇(Dihydrolinalool)、二氢月桂烯醇(Dihydromyrcenol)、二氢月桂烯醇(Dimyrcetol)、黑檀醇(Ebanol)、香叶醇(Geraniol)、异蒲勒醇(Isopulegol)、里哪醇(Linalool)、橙花醇(Nerol)、橙花叔醇(Nerolidol)、反式-2顺式-6壬二烯醇、聚檀香醇(Polysantol)、Rosalva、白雷曼檀香核(Sandalmysore core)、檀香(Sandalore)、萜烯-4-醇(Terpinen-4-ol)、萜品醇(Terpineol)、反式-2-己烯醇。
酚类,例如:丁羟茴醚、二氢丁香酚(Dihydroeugenol)、二甲基氢醌、二甲基间苯二酚、丁香酚纯(Eugenol pure)、愈创木酚、异丁香酚、间甲酚、甲基丹提力士(Methyldiantilis)、对甲酚、丙烯基乙基愈创木酚(Propenyl guaethol)、麝香草酚(Thymol)、香荚兰醇(Ultravanil)。
醚类,例如:降龙涎香醚(Ambroxan)、茴香脑(Anethole)、花药(Anther)、苄基异戊基醚、苄基异丙基醚、异戊酸苄酯、鸢尾香木(Boisiris)、柏木甲醚(Cedramber)、降龙涎醚(Cetalox)、癸基甲基醚、二苄基醚、二氢玫瑰氧化物、二苯醚(Diphenyl oxide)、道立米(Doremox)、草蒿脑(Estragole)、乙基芳樟醇、桉油精、佳乐麝香(Galaxolide)、吉兰吡喃(Gyrane)、Herbavert、酸橙氧化物(Lime oxide)、Madrox、甲基异丁香酚、萘基异丁基醚β、橙花醚(Nerol oxide)、萘乙醚(Nerolin bromelia)、对甲苯基丁醚、对甲苯基甲基醚、Petiole、苯基乙基甲基醚、2,4-二甲基-4-苯基呋喃(Rhubafuran)、玫瑰氧化物(Roseoxide)、芳香玫瑰醚(Rosyrane)、龙涎香醚(Trisamber)、Vetylbois K、萘基甲基醚(Yarayara)。
缩醛类,例如:乙缩醛CD、乙缩醛R、龙涎缩醛(Amberketal)、乙氧基环十二烷基甲烷(Boisambrene forte)、柠檬醛二乙缩醛(Citrathal)、1,1-二乙氧基乙烷、翠绿亚胺(Emeraldine)、Freshopal、薰衣草噁烷(Herboxane)、Indoflor、Jacinthaflor、Magnolan、香辣醚(Spirambrene)、苯乙醛二甲缩醛(Viridine)、爱林塔尔(Elintaal)、克力二噁茂烷(Glycolierral)、卡拉花醛(Karanal)、圆柚甲烷(Methyl pamplemousse)。
烃类,例如:红没药烯(Bisabolene)、莰烯、蒈烯δ3(Carene delta 3)、石竹烯(Caryophyllene)、柏木烯(Cedrene)、对伞花烃(Cymene para)、二戊烯(Dipentene)、二苯基甲烷、异长叶烯(Isolongifolene)、d-柠檬烯、长叶烯(Longifolene)、月桂烯(Myrcene)、萘、罗勒烯(Ocimene)、蒎烯α、蒎烯β、苯乙烯、萜品烯γ、萜品油烯(Terpinolene)、1,3,5-十一碳三烯、异丙基格篷(Verdoracine)。
硫化合物,例如:主体黑醋栗(Corps cassis)、二丁基硫醚、二甲基硫醚、2-己基-3-氧代环戊羧酸甲酯(Exovert)、西柚硫醇(Grapefruit thiol)、噁烷(Oxane)、巯基马来酮(Ribes mercaptan)、硫噻唑(Sulfurol)、桉叶硫醚(Thiocineol)。
腈类,例如:肉桂腈(Cinnamyl nitrile)、香茅腈(Citronellyl nitrile)、3.7-二甲基-6-辛烯腈(Citronitrile)、Clonal、枯茗腈(Cumin nitrile)、己基环戊酮、鸢尾腈、3,7-二甲基-2,6-辛二烯腈(Lemonile)、牡丹腈(Peonile)、十三烷基腈、Agrumen nitrile、正癸腈。
肟类,例如:二甲基二环辛酮肟(Buccoxime)、雷冰诺星(Labienoxime)、榄青酮(Stemone)。
氮杂环类,例如:2-乙酰吡嗪、2-乙酰吡啶、仲丁基喹啉、Corps racine、2-乙基-3,5(或6)-二甲基吡嗪、糠基吡咯、吲哚、异丁基喹啉、2-异丁基-3(或6)-甲氧基吡嗪、异丙基喹啉、Maritima、对甲基喹啉、3-甲基吲哚(Skatol)、2,3,5-三甲基吡嗪。
硝基化合物,例如:麝香酮(Musk Ketone)。
希夫碱类,例如:橙花素(Aurantiol)、半日花素(Helianthral)、女贞缩醛(Ligantraal)、玲兰素(Verdantiol)。
其他材料,例如:乙酰苯胺、环胺(Gardamide)、对苯二甲酰胺、邻氨基苯甲酸二甲基酯、邻氨基苯甲酸甲酯、正丁酸、癸酸、己酸、辛酸、苯基乙酸、石竹烯氧化物、环氧柏木醚(Cedroxyde)、Tobacarol。
因此,式(7)和/或(8)的化合物可用于生产组合物,以及从上述汇编中显而易见的是,可用于生产各种已知的气味剂/香味、风味和/或除臭/掩蔽材料。在这样的组合物的生产中,早先提及的已知的香味、风味和/或除臭/掩蔽材料可以根据香料商已知的方法使用,例如,根据W.A.Poucher,Perfumes,Cosmetics and Soaps 2,第7版,Chapman and Hall,伦敦1974。
在本发明的一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物除了式(7)和/或(8)的醇之外还包含至少一种酯和/或一种醇,优选至少酯和醇的混合物;所述酯和/或醇优选选自上文限定的列表。在本发明的一个实施方案中,要求保护的气味剂组合物的特征在于式(7)或式(8)的化合物与酯和/或其他醇的总含量大于25重量%,优选大于50重量%,例如大于75重量%,或甚至大于90重量%。
预期本公开的化合物的所有立体异构体,无论是混合物还是纯的或基本纯的形式。本公开的化合物可以在任何碳原子处有不对称中心,因此,要求保护的化合物可以对映体形式或非对映体形式存在,或以其混合物存在。制备方法可以利用外消旋体、(纯)对映体、对映体的非外消旋混合物、非对映体或非对映体的混合物作为起始材料。当非对映体或对映体产物作为混合物获得时,它们可以通过常规方法例如色谱分离或分级结晶来分离,或通过非对映体盐的形成来分离。在有意时,也可以通过遵循适当的对映选择性或非对映选择性反应来获得所需的对映体或非对映体。
在本发明的一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物除了式(7)或式(8)的醇之外还包含它们相应的式(5)或式(6)的母体酮。
母体化合物在这里被认为是作为合成中所用中间体的化合物。
本发明还涉及气味剂组合物,其包含式(7)的醇与它(它们)相应的式(5)的母体酮的混合物;在一个优选的实施方案中,式(5)的母体酮与其式(7)的醇之间的重量比为0.001至0.2,和/或式(7)的醇和它们相应的式(5)的母体酮在气味剂组合物中的总含量大于1重量%,例如大于25重量%,优选大于50重量%,例如大于75重量%,或甚至大于90重量%。
本发明还涉及气味剂组合物,其包含式(8)的醇与它(它们)相应的式(6)的母体酮的混合物;在一个优选的实施方案中,式(6)的母体酮与其式(8)的醇之间的重量比为0.001至0.2,和/或式(8)的醇和它们相应的式(6)的母体酮在气味剂组合物中的总含量大于1重量%,例如大于25重量%,优选大于50重量%,例如大于75重量%,或甚至大于90重量%。
在本发明的另一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物包含式(8)的醇和式(7)的醇的混合物。
本发明还涉及气味剂组合物,其包含式(7)的醇与式(8)的醇的混合物,任选且优选连同它们相应的式(5)/式(6)的母体酮;在一个优选的实施方案中,母体酮与其醇之间的重量比为0.001至0.2,和/或式(7)和式(8)的醇以及它们相应的式(5)和式(6)的母体酮在气味剂组合物中的总含量大于1重量%,例如大于25重量%,优选大于50重量%,例如大于75重量%,或甚至大于90重量%。
本发明还涉及气味剂组合物,其包含式(7d)的醇任选且优选与一种或多种式(7a-c)的醇和/或一种或多种其相应的式(5a-d)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(7c)的醇任选且优选与一种或多种式(7a-b)的醇和/或一种或多种其相应的式(5a-c)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(7b)的醇任选且优选与式(7a)的醇和/或一种或多种其相应的式(5a-b)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(7e)的醇任选且优选与式(7a)的醇和/或一种或多种其相应的式(5a,e)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(7f)的醇任选且优选与一种或多种式(7a-b)的醇和/或一种或多种其相应的式(5a-b,f)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8e)的醇任选且优选与式(8a)和/或(7a)的醇和/或其相应的式(6a)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8f)的醇任选且优选与式(8a)和/或(8b)和/或(7a)的醇和/或其相应的式(6f)和/或(6a)和/或(6b)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8f)的醇任选且优选与式(8b)和/或式(7b)和/或(7a)的醇和/或其相应的式(6f)和/或(6b)和/或(5b)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8c)的醇任选且优选与式(8b)和/或(8a)和/或(7a)的醇和/或其相应的式(6c)和/或(6b)和/或(6a)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8c)的醇任选且优选与式(8b)和/或(7b)和/或(7a)的醇和/或其相应的式(6c)和/或(6b)和/或(5b)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8c)的醇任选且优选与式(7c)和/或(7b)和/或(7a)的醇和/或其相应的式(6c)和/或(5c)和/或(5b)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8d)的醇任选且优选与式(8c)和/或(8b)和/或(8a)和/或(7a)的醇和/或其相应的式(6d)和/或(6c)和/或(6b)和/或(6a)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8d)的醇任选且优选与式(8c)和/或(8b)和/或(7b)和/或(7a)的醇和/或其相应的式(6d)和/或(6c)和/或(6b)和/或(5b)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8d)的醇任选且优选与式(8c)和/或(7c)和/或(7b)和/或(7a)的醇和/或其相应的式(6d)和/或(6c)和/或(5c)和/或(5b)和/或(5a)的母体酮一起的混合物。
本发明还涉及气味剂组合物,其包含式(8d)的醇任选且优选与式(7d)和/或(7c)和/或(7b)和/或(7a)的醇和/或其相应的式(6d)和/或(5d)和/或(5c)和/或(5b)和/或(5a)的母体酮一起的混合物。
作为提醒,式(7)和式(8)的醇可以有利地由以下图式表示
其中R是具有1至6个碳原子的烷基或具有2至6个碳原子的烯基。
作为提醒,式(5)或式(6)的酮可以有利地由以下图式表示
其中R是具有1至6个碳原子的烷基或具有2至6个碳原子的烯基。
本公开通过以下实施例进一步说明,这些实施例决不应被解释为进一步限制。本领域技术人员将容易地理解,所描述的具体方法和结果仅仅是说明性的。
合成实施例
实施例1:
4,4,5-三甲基己-5-烯-3-醇的合成:
步骤-1:4,4,5-三甲基己-5-烯-3-酮的合成:
在25℃下在氮气下,在搅拌的同时,将甲磺酸(886g,9.21mol)添加到2,3-二甲基-2-丁烯(2.58kg,30.7mol,1当量)和丙酸酐(3.99kg,30.7mol)的混合物中。将混合物在25℃下搅拌4小时。随后,混合物用水(1×2.00L)、然后11.7%碳酸钠水溶液(1×6.00kg)和水(1×2.00L)洗涤。粗产物通过真空蒸馏纯化,得到4,4,5-三甲基己-5-烯-3-酮(2.20kg,51%)。
1H NMR(400MHz,CDCl3):δ0.92(t,J=7.2Hz,3H),1.15(s,6H),1.56(s,3H),2.35(q,J=7.2Hz,2H),4.87(s,2H).
13C NMR(100MHz,CDCl3):δ8.3,20.1,23.3,29.5,53.5,111.4,148.0,214.4。
步骤-2:4,4,5-三甲基己-5-烯-3-醇的合成:
在20-25℃下,在搅拌的同时,经4小时的时间,将硼氢化钠(930g,24.5mol)添加到4,4,5-三甲基己-5-烯-3-酮(3.00kg,21.4mol)、乙醇(6.00kg)和水(1.50kg)的混合物中。然后将混合物在30℃下搅拌9小时。随后添加乙酸(400g)。分离有机相,且用水(3×9.00L)、10%碳酸钠水溶液(1×3.00L)和水(1×3.00L)洗涤。将粗产物(2.85kg)真空蒸馏(75-81℃/35毫巴),得到为无色液体的4,4,5-三甲基己-5-烯-3-醇(1.97g,65%)。
1H NMR(600MHz,CDCl3)δ1.01(s,3H),1.02(t,J=7.4Hz,3H),1.05(s,3H),1.26(tdd,J=14.1,9.5,7.3Hz,1H),1.52(tdd,J=15.1,7.5,1.7Hz,1H),1.75(s,3H),3.38(dd,J=10.4,1.7Hz,1H),4.84(s,1H),4.91(s,1H).13C NMR(151MHz,CDCl3)δ11.93,19.72,21.47,22.66,23.92,43.82,77.28,111.90,151.14。
实施例2:
4,4,5-三甲基己-3-醇的合成:
步骤-1:4,4,5-三甲基己-3-酮的合成:
在25℃下,将雷尼镍(400mg,6.80mmol)添加到4,4,5-三甲基己-5-烯-3-酮(50.0g,356mmol)在异丙醇(240mL)中的溶液中,并且在60℃/14巴的氢气下搅拌混合物48小时。将混合物冷却到25℃,通过硅藻土垫过滤,且减压除去溶剂,以得到4,4,5-三甲基己-3-酮(47.6g,94%)。
1H NMR(400MHz,CDCl3):δ0.72(d,J=7.2Hz,6H),0.93-0.97(m,9H),1.90-1.96(m,1H),2.39(q,J=7.2Hz,2H).13C NMR(100MHz,CDCl3):δ8.0,17.4,20.4,30.0,33.9,50.5,216.8。
步骤-2:4,4,5-三甲基己-3-醇的合成:
在20-25℃下,在搅拌的同时,经1小时的时间,将硼氢化钠(9.50g,253mmol)添加到4,4,5-三甲基己-3-酮(30.0g,210mmol)在乙醇(60.0mL)和水(15.0mL)中的混合物中。然后将混合物在30℃下搅拌9小时。随后添加乙酸(4.00g)。分离有机相,并用水(3×90.0mL)、10%碳酸钠水溶液(1×30.0mL)和水(1×30.0mL)洗涤。将粗产物真空蒸馏,得到为无色液体的4,4,5-三甲基己-3-醇(27.0g,90%)。
1H NMR(400MHz,CDCl3):δ0.64(s,3H),0.72(s,3H),0.73(d,J=6.0Hz,3H),0.78(d,J=6.8Hz,3H),0.93(t,J=7.2Hz,3H),1.10-1.19(m,1H),1.44-1.54(m,1H),1.62-1.70(m,1H),1.84(s,1H),3.25(dd,J=10.4Hz&1.6Hz,1H).13C NMR(100MHz,CDCl3):δ10.0,16.3,16.5,16.8,17.0,22.0,30.7,37.8,76.8。
实施例3:
3,3,4-三甲基戊-4-烯-2-醇的合成:
步骤1:3,3,4-三甲基戊-4-烯-2-酮的合成:
在5℃下在氮气下,在搅拌的同时,将甲磺酸(171g,1.77mol)添加到2,3-二甲基-2-丁烯(510g,5.94mol)和乙酸酐(520g,5.94mol)的混合物中。在冰浴中搅拌混合物,并留置以在24小时内达到20℃。随后添加水(1.50L),并用甲基叔丁基醚(3×500mL)提取混合物。合并的有机相依次用水(2×750mL)、饱和碳酸钠水溶液(直至pH 7)和盐水(750mL)洗涤。将有机相用Na2SO4干燥,并且减压除去挥发物。将残余物(960g)真空蒸馏,得到3,3,4-三甲基戊-4-烯-2-酮(501g,66%)。
1H NMR(400MHz,CDCl3):δ1.15(s,6H),1.58(s,3H),1.98(s,3H),4.89(s,2H).
13C NMR(100MHz,CDCl3):δ19.2,22.2,23.9,53.0,110.6,146.8,210.9。
步骤2:3,3,4-三甲基戊-4-烯-2-醇的合成:
在20-25℃下,在搅拌的同时,经1小时,将硼氢化钠(60.0g,1.58mol)添加到3,3,4-三甲基戊-2-酮(200g,1.58mol)在乙醇(400mL)和水(200mL)中的混合物中。然后将混合物在30℃下搅拌2小时。随后添加饱和氯化铵水溶液,且用乙酸乙酯(3×300mL)提取混合物。混合的提取物用水(3×90.0mL)、10%碳酸钠水溶液(1×300mL)和水(1×300mL)洗涤。减压除去挥发物,并将残余物(285g)真空蒸馏(27-30℃/30毫巴),得到为无色液体的3,3,4-三甲基戊-4-烯-2-醇(168g,83%)。
1H NMR(600MHz,CDCl3):δ1.00(s,3H),1.05(s,3H),1.10(d,J=6.4Hz,3H),1.68(s,1H),1.76(s,3H),3.74(q,J=6.3Hz,1H),4.86(d,J=0.7Hz,1H),4.96-4.90(m,1H).
13C NMR(151MHz,CDCl3)δ16.6,19.6,20.5,22.7,43.6,70.9,112.0,150.9。
实施例4:
3,3,4-三甲基戊-2-醇的合成:
步骤1:3,3,4-三甲基戊-2-酮的合成:
将雷尼镍(3.48g,59.4mmol)添加到3,3,4-三甲基戊-4-烯-2-酮(150g,1.18mol)在甲醇(300mL)中的溶液中,并且将反应器用氮气冲洗。然后将混合物在60℃/21巴的氢气氛下搅拌72小时。随后将混合物冷却至25℃并通过硅藻土垫过滤。用甲醇(100mL)洗涤滤饼。合并的滤液用硫酸钠(152g)干燥,并且减压除去挥发物,以得到3,3,4-三甲基戊-2-酮(140g,91.8%)。
1H NMR(400MHz,CDCl3):δ0.75(d,J=6.8Hz,6H),0.95(s,6H),1.88-1.98(m,1H),2.04(s,3H).
13C NMR(100MHz,CDCl3):δ17.4,20.2,25.0,33.7,50.8,214.2。
步骤2:3,3,4-三甲基戊-2-醇的合成:
在0-5℃下,在搅拌的同时,经1小时的时间,将硼氢化钠(42.3g,1.12mmol)添加到3,3,4-三甲基戊-2-酮(152g,1.19mol)、甲醇(400mL)和水(22.8mL)的混合物中。然后将混合物在25℃下搅拌24小时。随后在25℃下经15分钟的时间添加硼氢化钠(10.6g,280mmol)且将混合物再搅拌21小时。然后在5-10℃下添加10%盐酸水溶液直至pH 7。随后,在50℃下减压除去挥发物,并添加水(150mL)。用二氯甲烷(3×150mL)提取混合物。合并的有机相用盐水(1×100mL)洗涤,且用硫酸钠(15g)干燥。在40℃下减压除去挥发物,以得到为无色液体的3,3,4-三甲基戊-2-醇(125g,80.7%)。
1H NMR(400MHz,CDCl3):δ0.63(s,3H),0.73(s,3H),0.76(d,J=8.0Hz,3H),0.78(d,J=6.8Hz,3H),1.03(d,J=6.4Hz,3H),1.55-1.66(m,1H),1.95-1.96(bs,1H),3.66(q,J=6.4Hz,1H).
13C NMR(100MHz,CDCl3):δ17.2,17.9,18.7,32.5,39.4,71.9。
实施例5:
2,3,3-三甲基辛-1-烯-4-醇的合成的合成:
步骤1:2,3,3-三甲基辛-1-烯-4-酮的合成
在搅拌的同时,经30分钟的时间,将甲磺酸(48.0g,499mmol)添加到戊酸酐(310g,1.66mol)和2,3-二甲基丁-2-烯(140g,1.66mol)的混合物中。然后,将混合物在40℃下搅拌28小时。随后在25℃下添加15%碳酸钾水溶液(1.33L),并将混合物搅拌30分钟。分离有机相,且用水(4×300ml)洗涤直至pH 7。将粗产物(204g)真空蒸馏(70-75℃/12毫巴),以得到为无色液体的2,3,3-三甲基辛-1-烯-4-酮(104g,37.1%)。
1H NMR(400MHz,CDCl3):δ0.81(t,J=7.2Hz,3H),1.15-1.24(m,8H),1.39-1.46(m,2H),1.57(s,3H),2.32(t,J=7.6Hz,2H),4.88(s,2H).
13C NMR(100MHz,CDCl3):δ14.0,20.3,22.5,23.4,26.4,36.2,53.8,111.7,148.1,214.0。
步骤2:2,3,3-三甲基辛-1-烯-4-醇的合成:
在30℃下,在搅拌的同时,经30分钟的时间,将硼氢化钠(8.57g,232mmol)添加到2,3,3-三甲基辛-1-烯-4-酮(51.0g,29.0mmol)在乙醇(50.0mL)和THF(50.0mL)中的溶液中。然后将混合物在65℃下搅拌14小时。随后在25℃下添加5%盐酸水溶液(40mL)。分离有机相,且用乙酸乙酯(1×200mL)提取水相。合并的有机相用水(4×100mL)洗涤,且减压除去挥发物。将粗产物(49.0g)真空蒸馏(85-89℃/10毫巴),以得到为无色液体的2,3,3-三甲基辛-1-烯-4-醇(42.9g,87.1%)。
1H NMR(600MHz,CDCl3):δ0.91(t,J=7.2Hz,3H),1.01(s,3H),1.05(s,3H),1.39-1.21(m,4H),1.47-1.41(m,1H),1.62-1.52(m,2H),1.75(s,3H),3.48-3.44(m,1H),4.84(s,1H),4.91(s,1H).
13C NMR(151MHz,CDCl3):δ14.1,19.7,21.4,22.6,22.8,29.6,30.7,43.8,75.5,111.9,151.1。
实施例6:
2,3,3-三甲基辛-4-醇的合成:
步骤-1:2,3,3-三甲基辛-4-酮的合成:
将雷尼镍(1.93g,32.0mmol)添加到2,3,3-三甲基辛-1-烯-4-酮(120g,660mmol)在异丙醇(200mL)中的溶液中,并且将高压釜用氮气冲洗。然后将混合物在50℃/7巴的氢气氛下搅拌13小时。将混合物冷却到25℃,通过硅藻土垫过滤,并将滤饼用异丙醇(50mL)洗涤。将滤液用硫酸钠(152g)干燥,且减压除去挥发物,以得到为无色液体的2,3,3-三甲基辛-4-酮(105g,83%)。
1H NMR(400MHz,CDCl3):δ0.72(d,J=7.2Hz,6H),0.83(t,J=7.6Hz,3H),0.93(s,6H),1.13-1.27(m,2H),1.42-1.49(m,2H),1.90-1.97(m,1H),2.36(t,J=7.6Hz,2H).
13C NMR(100MHz,CDCl3):δ13.9,17.5,20.3,22.4,26.0,33.7,36.6,50.6,216.3。
步骤-2:2,3,3-三甲基辛-4-醇的合成:
在30℃下,在搅拌的同时,经30分钟的时间,将硼氢化钠(6.48g,175mmol)添加到2,3,3-三甲基辛-4-酮(42.0g,219mmol)在乙醇(150mL)中的溶液中。然后将混合物在75℃下搅拌12小时。随后在30℃下添加乙酸乙酯(200ml),接着添加0.5N盐酸水溶液(40ml)。分离有机相,用水(4×100mL)洗涤,且减压除去挥发物,以得到2,3,3-三甲基辛-4-醇(39.5g,97%)
1H NMR(600MHz,CDCl3):δ3.44(d,J=7.9Hz,1H),1.77-1.67(m,1H),1.61-1.47(m,2H),1.41-1.19(m,6H),0.92(t,J=7.2Hz,3H),0.86(d,J=6.9Hz,3H),0.82(d,J=6.9Hz,3H),0.81(s,3H),0.72(s,3H).
13C NMR(151MHz,CDCl3):δ14.1,17.2,17.6,18.4,18.8,22.8,29.4,30.9,32.8,39.5,76.8。
实施例7:
2,3,3-三甲基壬-1-烯-4-醇的合成:
步骤-1:2,3,3-三甲基壬-1-烯-4-酮的合成:
在搅拌的同时,经30分钟的时间,将甲磺酸(27.9g,290mmol)添加到己酸酐(208g,970mmol)和2,3-二甲基丁-2-烯(85.5g,970mmol)的混合物中。然后将混合物在40℃下搅拌18小时。随后在25℃下添加15%碳酸钠水溶液(60.0g),并将混合物搅拌30分钟。分离有机相,且用乙酸乙酯(2×300mL)提取水相。合并的有机相用水(4×300ml)洗涤至pH 7,且减压除去挥发物。将粗产物真空蒸馏(75-84℃/6毫巴),以得到2,3,3-三甲基壬-1-烯-4-酮(68.2g,38.5%)。
1H NMR(400MHz,CDCl3):δ0.80(t,J=7.2Hz,3H),1.15-1.25(m,10H),1.40-1.48(m,2H),1.56(s,3H),2.32(t,J=7.6Hz,2H),4.87(s,2H).
13C NMR(100MHz,CDCl3):δ14.0,20.3,22.6,23.4,23.9,31.6,36.4,53.8,111.7,148.1,214.0。
步骤-2:2,3,3-三甲基壬-1-烯-4-醇的合成:
在30℃下,在搅拌的同时,经30分钟的时间,将硼氢化钠(4.03g,109mmol)添加到2,3,3-三甲基壬-1-烯-4-酮(35.0g,182mmol)在乙醇(90.0ml)中的溶液中。然后将混合物在65℃下搅拌9小时。随后在30℃下添加乙酸乙酯(150ml),接着添加0.5N盐酸水溶液(40.0ml)。分离的有机相用水(4×80.0mL)洗涤,且减压除去挥发物,以得到为无色液体的2,3,3-三甲基壬-1-烯-4-醇(34.0g,96%)。
1H NMR(600MHz,CDCl3):δ0.90(t,J=7.0Hz,3H),1.01(s,3H),1.05(s,3H),1.36-1.21(m,6H),1.46-1.40(m,1H),1.54(s,J=18.5Hz,1H),1.63-1.56(m,1H),1.75(d,J=0.7Hz,3H),3.48-3.44(m,1H),4.84(d,J=0.9Hz,1H),4.93-4.89(m,1H).
13C NMR(151MHz,CDCl3):δ14.10,19.71,21.47,22.61,22.73,27.13,31.01,32.03,43.79,75.53,111.91,151.13。
实施例8:
2,3,3-三甲基壬-4-醇的合成
步骤-1:2,3,3-三甲基壬-4-酮的合成:
将雷尼镍(2.03g,34.0mmol)添加到2,3,3-三甲基壬-1-烯-4-酮(135g,690mmol)在异丙醇(207mL)中的溶液中,并且将高压釜用氮气冲洗。然后将混合物在50℃/7巴的氢气氛下搅拌5小时。将混合物冷却至25℃并通过硅藻土垫过滤。用异丙醇(50.0mL)洗涤滤饼。将合并的滤液用硫酸钠(150g)干燥,且减压除去挥发物,以得到为无色液体的2,3,3-三甲基辛-4-酮(128g,94.8%)。
1H NMR(400MHz,CDCl3):δ0.73(d,J=6.8Hz,6H),0.81(t,J=7.2Hz,3H),0.93(s,6H),1.13-1.27(m,4H),1.44-1.51(m,2H),1.90-1.97(m,1H),2.35(t,J=7.6Hz,2H).
13C NMR(100MHz,CDCl3):δ13.8,17.4,20.3,22.5,23.5,31.5,33.7,36.8,50.5,216.1。
步骤-2:2,3,3-三甲基壬-4-醇的合成:
在30℃下,在搅拌的同时,经30分钟的时间,将硼氢化钠(13.6g,369mmol)添加到2,3,3-三甲基壬-4-酮(60.0g,307mmol)在乙醇(225mL)中的溶液中。然后将混合物在78℃下搅拌29小时。随后在30℃下添加乙酸乙酯(300ml),接着添加0.5N盐酸水溶液(60.0ml)。分离的有机相用水(4×150mL)洗涤,且减压除去挥发物。将粗产物真空蒸馏(90-103℃/11毫巴),以得到为无色液体的2,3,3-三甲基壬-4-醇(50.8g,89%)。
1H NMR(600MHz,CDCl3)δ0.72(s,3H),0.81(s,3H),0.82(d,J=6.9Hz,3H),0.86(d,J=6.9Hz,3H),0.90(t,J=7.0Hz,3H),1.38-1.19(m,7H),1.49(ddd,J=9.2,6.3,2.4Hz,1H),1.63-1.53(m,1H),1.77-1.68(m,1H),3.47-3.41(m,1H).
13C NMR(151MHz,CDCl3)δ14.1,17.2,17.6,18.4,18.8,22.7,26.9,31.2,32.0,32.8,39.5,76.9。
实施例9:
2,4,4,5-四甲基己-5-烯-3-醇的合成
步骤-1:2,4,4,5-四甲基己-5-烯-3-酮的合成:
在0℃下,在氮气氛下,经40分钟的时间,将2-甲基丙-2-醇钾(54.0g,481mmol)添加到4,4,5-三甲基己-5-烯-3-酮(45.0g,321mmol)在四氢呋喃(1.80L)中的溶液中。然后将混合物在0-5℃下搅拌30分钟。随后,滴加碘甲烷(49.9mL,802mmol),然后将混合物在25℃下搅拌16小时。添加氯化铵饱和水溶液,且用乙酸乙酯(2×200mL)提取混合物。合并的有机相用无水Na2SO4干燥,且减压除去挥发物。使用ss-无规填充柱(0.3m)通过分馏来纯化粗产物(65.6g),以得到为无色液体的2,4,4,5-四甲基己-5-烯-3-酮(36.2g,65.8%)。
1H NMR(600MHz,CDCl3):δ1.00(d,J=6.7Hz,6H),1.25(s,6H),1.66(s,3H),3.03-3.11(m,1H),5.00(brd,J=7.1Hz,1H).
13C NMR(151MHz,CDCl3):δ20.6,20.8,23.1,34.0,54.4,112.3,147.3,218.2.
步骤-2:2,4,4,5-四甲基己-5-烯-3-醇的合成:
在0℃下,经2小时的时间,将硼氢化钠(14.72g,389mmol)添加到2,4,4,5-四甲基己-5-烯-3-酮(15.0g,97.0mmol)在甲醇(200ml)中的溶液中。然后将混合物在0℃下搅拌2小时,且在25℃下搅拌12小时。随后,在0℃下添加5%盐酸水溶液直至pH 7。用乙酸乙酯(3×50mL)提取混合物。合并有机相,减压(50℃/225毫巴)除去挥发物。粗产物(15.3g)通过硅胶色谱法使用正己烷/乙酸乙酯(80/20)作为洗脱剂纯化,以得到为无色混合物的2,4,4,5-四甲基己-5-烯-3-醇(12.2g,73.6%)。
1H NMR(600MHz,CDCl3):δ0.85(d,J=6.8Hz,3H),0.93(d,J=6.8Hz,3H),0.99(s,3H),1.01(s,3H),1.69(s,3H),1.73-1.82(m,1H),3.27(d,J=3.2Hz,1H),4.78(s,1H),4.76-4.80(m,1H),
13C NMR(151MHz,CDCl3):δ17.4,19.7,22.5,23.6,23.8,28.8,44.5,79.6,111.5,151.6。
实施例10:
2,3,3-三甲基庚-1-烯-4-醇的合成:
步骤-1:2,3,3-三甲基庚-1-烯-4-酮的合成:
在5℃下在氮气氛下,在搅拌的同时,将2,3-二甲基-2-丁烯(930g,11.0mol)添加到氯化锌(452g,3.31mol)在丁酸酐(1.75kg,11.0mol)中的溶液中。然后在6小时内将混合物温热至20℃,然后在20℃下搅拌48小时。随后添加水(4.00L)。分离的有机相用水(1×4.00L)、饱和碳酸钠水溶液(至pH 7)和盐水(1.00L)洗涤。粗产物(1.55kg)通过真空蒸馏(53-55℃/10毫巴)纯化,以得到为无色液体的2,3,3-三甲基庚-1-烯-4-酮(1.24kg,60%)。
1H NMR(400MHz,CDCl3):δ0.80(t,J=7.6Hz,3H),1.15(s,6H),1.43-1.52(m,2H),1.55(s,3H),2.31(t,J=7.2Hz,2H),4.88(s,2H).
13C NMR(151MHz,CDCl3):δ11.2,14.9,17.6,20.2,20.8,35.8,51.1,109.1,145.5,211.1。
步骤-2:2,3,3-三甲基庚-1-烯-4-醇的合成:
用20分钟将硼氢化钠(590mg,16.0mmol)添加到2,3,3-三甲基庚-1-烯-4-酮(2.00g,13.0mmol)在甲醇(20.0ml)中的溶液中。然后,在25℃下搅拌混合物6小时。随后添加5%盐酸水溶液直至pH 7。用乙酸乙酯(3×50mL)提取混合物,且将合并的提取物用水(50mL)洗涤。减压除去挥发物,以得到为无色液体的2,3,3-三甲基庚-1-烯-4-醇(1.92g,85%)。
1H NMR(400MHz,CDCl3):δ0.86(t,J=7.2Hz,3H),0.93(s,3H),0.97(s,3H),1.13-1.35(m,4H),1.60(bs,1H),1.67(s,3H),3.38-3.41(m,1H),4.77(d,J=0.4Hz,1H),4.82-4.83(m,1H).
13C NMR(151MHz,CDCl3):δ14.1,19.8,20.2,21.5,22.3,33.2,43.5,75.0,111.8,151.1。
实施例11:
(E)-2,3,3-三甲基庚-1,5-二烯-4-醇的合成:
步骤-1:(E)-2,3,3-三甲基庚-1,5-二烯-4-酮的合成:
在-5℃下,将氯化锌(300g,2.20mol)分批添加到巴豆酸酐(1.26kg,8.15mol)在甲基环己烷(500g)中的溶液中,并将混合物搅拌20分钟。然后在-5℃下经4小时的时间添加2,3-二甲基丁-2-烯(618g,7.34mol)。将混合物在25℃下搅拌16小时。随后添加水(1.50L)。分离的有机相用10%氢氧化钠水溶液(2.50L)、水(900mL)和盐水(600mL)洗涤,且减压除去挥发物。粗产物通过真空蒸馏(38-43℃/2毫巴)纯化,以得到为无色液体的(E)-2,3,3-三甲基庚-1,5-二烯-4-酮(469g,42%)。
1H NMR(400MHz,CDCl3):δ1.15(s,6H),1.56-1.57(m,3H),1.77(dd,J=6.8,1.6Hz,3H),4.89-4.92(m,2H),6.31(dq,J=15.2,1.6Hz,1H),6.83-6.91(m,1H).
13C NMR(151MHz,CDCl3):δ17.8,20.2,23.02,53.0,111.9,126.1,142.1,148.1,203.9。
步骤-2:(E)-2,3,3-三甲基庚-1,5-二烯-4-醇的合成:
在25℃下将七水合氯化铈(III)(2.47g,6.63mmol)添加到(E)-2,3,3-三甲基庚-1,5-二烯-4-酮(1.00g,6.57mmol)在甲醇(50.0ml)中的溶液中。将混合物在25℃下搅拌30分钟。随后,在0℃下添加硼氢化钠(249mg,6.57mmol),且将混合物在0℃下搅拌2小时。添加水(100mL),且用二氯甲烷(3×50mL)提取混合物。合并的有机提取物用硫酸钠干燥,且减压除去挥发物。粗产物(967mg)通过硅胶柱色谱法使用正己烷/乙酸乙酯混合物(80/20)作为洗脱剂纯化,以得到为无色液体的(E)-2,3,3-三甲基庚-1,5-二烯-4-醇(890mg,84%)。
1H NMR(400MHz,CDCl3):δ0.89(s,3H),0.98(s,3H),1.64-1.67(m,4H),1.70(d,J=0.8Hz,3H),3.85-3.87(m,1H),4.80(d,J=0.8Hz,1H),4.87-4.88(m,1H),5.37-5.44(m,1H),5.59-5.67(m,1H).
13C NMR(151MHz,CDCl3):δ15.4,17.8,18.9,21.4,41.8,75.1,110.3,126.7,127.9,148.8。
实施例12:
2,3,3,5-四甲基庚-1-烯-4-醇的合成:
步骤-1:2,3,3,5-四甲基庚-1-烯-4-酮的合成:
在氮气氛下,在10℃下,经15分钟的时间,将2-甲基丙-2-醇钾(8.40g,74.9mmol)添加到4,4,5-三甲基己-5-烯-3-酮(5.00g,35.7mmol)在四氢呋喃(50.0ml)中的溶液中。然后滴加碘乙烷(11.1g,71.3mmol),且令混合物温热至25℃并搅拌24小时。随后添加饱和氯化铵水溶液(50mL),且用甲基叔丁基醚(2×50.0mL)提取混合物。合并的有机提取物经无水硫酸钠干燥,且减压除去挥发物,以得到为无色液体的2,3,3,5-四甲基庚-1-烯-4-酮(6.30g,90%)。
1H NMR(400MHz,CDCl3):δ0.75(t,J=7.6Hz,3H),0.90(d,J=6.8Hz,3H),1.16(s,3H),1.18(s,3H),1.20-1.28(m,1H),1.38-1.50(m,1H),1.57(s,3H),2.72-2.84(m,1H),4.90(s,2H).13C NMR(100MHz,CDCl3):δ10.8,17.2,19.7,22.3,22.4,26.5,40.0,53.4,111.6,146.2,216.3。
步骤-2:2,3,3,5-四甲基庚-1-烯-4-醇的合成:
在25℃下,将硼氢化钠(340mg,8.91mmol)缓慢添加到2,3,3,5-四甲基庚-1-烯-4-酮(1.00g,5.94mmol)在甲醇(5.00mL)中的溶液中,且将混合物在25℃下搅拌20小时。随后,添加0.5N盐酸水溶液(10.0mL)直至pH 7,且用乙酸乙酯(2×10mL)提取混合物。合并的有机相用水(2×20mL)洗涤,且减压除去挥发物,以得到为无色液体的2,3,3,5-四甲基庚-1-烯-4-醇(1.10g,86%)(非对映体的混合物)。
1H NMR(400MHz,CDCl3):δ0.75-0.85(m,6H),0.96-1.01(m,6H),1.21-1.35(m,1H),1.40-1.56(m,3H),1.69(s,3H),3.30(d,J=1.6Hz,0.5H),3.37(d,J=1.6Hz,0.5H),4.71(s,1H),4.79-4.81(m,1H).13C NMR(100MHz,CDCl3):δ10.87,13.01,17.2,22.0,23.3,33.8,35.2,43.4,78.6,110.5,150.6。
实施例13:
(E)-2,3,3-三甲基庚-1,5-二烯-4-醇的供选合成:
步骤-1:(E)-2,3,3-三甲基庚-1,5-二烯-4-酮的供选合成:
在-20℃下在氮气氛下,将2,3-二甲基-1-丁烯(284g,405mL,3.38mol)添加到三氟甲磺酸(5.07g,3.0mL,33.8mmol)在巴豆酸酐(521g,500mL,3.38mol)中的溶液中。然后将混合物在0℃下搅拌30分钟,且在20℃下搅拌12小时。随后,添加2M氢氧化钠水溶液(2.53L,5.07mol),将混合物在氮气氛下在50℃下搅拌4小时,并冷却到20℃。然后分离有机部分,且用甲基叔丁基醚(2.00L)提取水性部分。将合并的有机部分用盐水洗涤,且经硫酸钠干燥。减压除去挥发物,且将残余物真空蒸馏(50-52℃/4毫巴),以得到2,3,3,6-三甲基庚-1,5-二烯-4-酮(142g,22%产率)。
步骤-2:(E)-2,3,3-三甲基庚-1,5-二烯-4-醇的合成:参见实施例11下面给出了选择的上述化合物的嗅觉性质:
组合物实施例
在以下发明实施例(A)和比较例(B/C/D)中,将实施例1的化合物和商业化合物包括在柑橘调香味中用于洗发剂(E=空白)。DPG=二丙二醇。
不同化合物的比较研究,其中E栏是空白:
引入0.1重量%的4,4,5-三甲基己-5-烯-3-醇增强了柑橘效果,赋予香味更闪耀和更天然和更清新的特性(A)。
与这种材料相比,用参考材料观察到以下效果:
引入0.1%重量的冰片使这种柑橘调更有松香,虽然合成效果显著(B)。
引入0.1重量%的乙酸异冰片酯对这种柑橘调没有明显的影响(C)。
引入0.1%重量的乙酸小茴香酯使这种柑橘调更有松香和稍微薄荷味效果,但没有组合物A的天然和清新特性(D)。
Claims (18)
2.根据权利要求1所述的香味、风味和/或除臭/掩蔽组合物,其中R是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-甲基丙-1-烯-2-基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
3.根据权利要求2所述的香味、风味和/或除臭/掩蔽组合物,其中
-对于所述式(7)的化合物,R不能是甲基、异丙基或异丁基,并且
-所述式(7)的化合物不能是2,3,3,5,5,6-六甲基庚-1,6-二烯-4-醇或2,3,3,6,7-五甲基辛-1,6-二烯-4-醇,并且
-对于所述式(8)的化合物,R不能是甲基、异丙基或乙烯基。
5.根据前述权利要求中任一项所述的香味、风味和/或除臭/掩蔽组合物,其中式(7)和/或式(8)的化合物的含量在0.00001重量%和99.9重量%之间,例如在0.0001重量%和95重量%之间。
6.根据前述权利要求中任一项所述的香味、风味和/或除臭/掩蔽组合物,其另外包含至少一种酯和/或一种其他醇,优选至少酯和其他醇的混合物。
7.根据前述权利要求所述的香味、风味和/或除臭/掩蔽组合物,其中式(7)和/或式(8)的化合物与所述酯和/或其他醇的总含量大于25重量%,优选大于50重量%,例如大于75重量%,或甚至大于90重量%。
8.根据前述权利要求中任一项所述的香味、风味和/或除臭/掩蔽组合物,其包含至少一种式(7)的醇和一种式(8)的醇的混合物。
11.根据权利要求9或10所述的香味、风味和/或除臭/掩蔽组合物,其中所述母体酮与其醇之间的重量比在0.001和0.2之间。
13.根据权利要求12所述的可用于香味、风味和/或除臭/掩蔽组合物的醇,其中所述醇选自式(7)或式(8)的化合物
其中
-对于所述式(7)的化合物,R是乙基、正丙基、正丁基、仲丁基、叔丁基、正戊基、2-甲基丙-1-烯-2-基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基,并且
-对于所述式(8)的化合物,R是乙基、正丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
14.根据权利要求13所述的醇,其中
-对于所述式(7)的化合物,R是乙基、正丙基、正丁基、正戊基、正己基、乙烯基、1-丙烯基、1-丁烯基、1-戊烯基或1-己烯基,并且
-对于所述式(8)的化合物,R是乙基、正丙基、正丁基、正戊基、正己基、1-丙烯基、1-丁烯基、1-戊烯基或1-己烯基。
16.式(7)或式(8)的化合物的制备
其中R是具有1至6个碳原子的烷基或具有2至6个碳原子的烯基,
其中
-所述式(7)的化合物通过以下连续步骤制备:
○使2,3-二甲基丁烯进行酰化合成步骤,任选随后进行烷基化步骤,以形成式(5)的不饱和酮化合物,其中所述不饱和酮化合物的基团R与所制备的式(7)的化合物的基团R相同,以及
○使所述不饱和酮化合物进行还原步骤以形成所述式(7)的醇化合物,并且
-所述式(8)的化合物通过以下连续步骤制备:
○使2,3-二甲基丁烯进行酰化合成步骤,任选地随后进行烷基化步骤,以形成式(5)的不饱和酮化合物,其中所述不饱和酮化合物的基团R与所制备的式(8)的化合物的基团R相同,以及
○使所述式(5)的不饱和酮化合物进行氢化步骤以形成式(6)的饱和酮化合物,以及
○使所述式(6)的饱和酮化合物进行还原步骤以形成所述式(8)的醇化合物,
-其中所述式(5)和式(6)的酮化合物由下列图式表示
17.根据权利要求1至10中任一项所述的香味、风味和/或除臭/掩蔽组合物在加香或调味产品中的用途。
18.根据权利要求11至15中任一项所述的醇在加香或调味产品中的用途。
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