CN104710283B - 环戊醇化合物 - Google Patents
环戊醇化合物 Download PDFInfo
- Publication number
- CN104710283B CN104710283B CN201410756658.5A CN201410756658A CN104710283B CN 104710283 B CN104710283 B CN 104710283B CN 201410756658 A CN201410756658 A CN 201410756658A CN 104710283 B CN104710283 B CN 104710283B
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- China
- Prior art keywords
- cyclopentanol
- methyl
- product
- fragrance
- ethyl
- 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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- -1 Cyclopentanol compound Chemical class 0.000 title claims description 36
- 239000003205 fragrance Substances 0.000 claims abstract description 56
- 239000002304 perfume Substances 0.000 claims abstract description 15
- 230000008859 change Effects 0.000 claims abstract description 9
- 239000004744 fabric Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 50
- 238000009472 formulation Methods 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 15
- 239000003599 detergent Substances 0.000 claims description 14
- 239000002781 deodorant agent Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 8
- 239000000344 soap Substances 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- FZTYLVFSULCDQI-UHFFFAOYSA-N 1-ethyl-2-pentylcyclopentan-1-ol Chemical compound C(C)C1(C(CCC1)CCCCC)O FZTYLVFSULCDQI-UHFFFAOYSA-N 0.000 claims description 5
- JYWIJCPAYPPHSW-UHFFFAOYSA-N 1-methyl-2-(3-methylbutyl)cyclopentan-1-ol Chemical compound CC1(C(CCC1)CCC(C)C)O JYWIJCPAYPPHSW-UHFFFAOYSA-N 0.000 claims description 5
- FMXAEOBMFNHGDX-UHFFFAOYSA-N 1-methyl-2-pentylcyclopentan-1-ol Chemical compound CC1(C(CCC1)CCCCC)O FMXAEOBMFNHGDX-UHFFFAOYSA-N 0.000 claims description 5
- SFKWXVLCKLVKFE-UHFFFAOYSA-N 1-ethyl-2-(3-methylbutyl)cyclopentan-1-ol Chemical compound C(C)C1(C(CCC1)CCC(C)C)O SFKWXVLCKLVKFE-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002386 air freshener Substances 0.000 claims description 4
- 239000012459 cleaning agent Substances 0.000 claims description 4
- 239000000645 desinfectant Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 230000037123 dental health Effects 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000834 fixative Substances 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 230000036541 health Effects 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 230000000474 nursing effect Effects 0.000 claims description 2
- 235000016709 nutrition Nutrition 0.000 claims description 2
- 230000035764 nutrition Effects 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 239000003292 glue Substances 0.000 claims 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 abstract description 10
- 230000006872 improvement Effects 0.000 abstract description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 74
- 239000000047 product Substances 0.000 description 39
- 238000005160 1H NMR spectroscopy Methods 0.000 description 37
- 238000009835 boiling Methods 0.000 description 20
- 230000035943 smell Effects 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 235000013599 spices Nutrition 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- VNWOJVJCRAHBJJ-UHFFFAOYSA-N 2-pentylcyclopentan-1-one Chemical compound CCCCCC1CCCC1=O VNWOJVJCRAHBJJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229930183419 Irisone Natural products 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 4
- YZKUNNFZLUCEET-RMKNXTFCSA-N (2e)-2-pentylidenecyclopentan-1-one Chemical compound CCCC\C=C1/CCCC1=O YZKUNNFZLUCEET-RMKNXTFCSA-N 0.000 description 3
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 3
- 235000000484 citronellol Nutrition 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- XCIXKGXIYUWCLL-HOSYLAQJSA-N cyclopentanol Chemical class O[13CH]1CCCC1 XCIXKGXIYUWCLL-HOSYLAQJSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- XEJGJTYRUWUFFD-FNORWQNLSA-N (e)-1-(2,6,6-trimethyl-1-cyclohex-3-enyl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1C(C)C=CCC1(C)C XEJGJTYRUWUFFD-FNORWQNLSA-N 0.000 description 2
- CHOOCIQDWNAXQQ-UHFFFAOYSA-N 1,5,5-trimethylcyclohexene Chemical compound CC1=CCCC(C)(C)C1 CHOOCIQDWNAXQQ-UHFFFAOYSA-N 0.000 description 2
- OHIIGLSGZTXTBM-UHFFFAOYSA-N 1,5,5-trimethylcyclopentene Chemical compound CC1=CCCC1(C)C OHIIGLSGZTXTBM-UHFFFAOYSA-N 0.000 description 2
- YBUIAJZFOGJGLJ-SWRJLBSHSA-N 1-cedr-8-en-9-ylethanone Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=C(C(C)=O)C2 YBUIAJZFOGJGLJ-SWRJLBSHSA-N 0.000 description 2
- OEUDHFWMZOYHKW-UHFFFAOYSA-N 1-cyclopentyl-2-ethylcyclopentane Chemical group C(C)C1CCCC1C1CCCC1 OEUDHFWMZOYHKW-UHFFFAOYSA-N 0.000 description 2
- WAWRWWQBGNCUPO-UHFFFAOYSA-N 1-cyclopentyl-2-methylcyclopentane Chemical group CC1CCCC1C1CCCC1 WAWRWWQBGNCUPO-UHFFFAOYSA-N 0.000 description 2
- WBFLMNGRXLEAHM-UHFFFAOYSA-N 1-ethenyl-2-(3-methylbutyl)cyclopentan-1-ol Chemical group CC(CCC1C(CCC1)(O)C=C)C WBFLMNGRXLEAHM-UHFFFAOYSA-N 0.000 description 2
- QVBWFULKXITEOM-UHFFFAOYSA-N 1-ethyl-2-heptylcyclopentan-1-ol Chemical group C(C)C1(C(CCC1)CCCCCCC)O QVBWFULKXITEOM-UHFFFAOYSA-N 0.000 description 2
- WFYASMDBKAJRKY-UHFFFAOYSA-N 1-methyl-2-(2-methylpentyl)cyclopentan-1-ol Chemical group CC1(C(CCC1)CC(CCC)C)O WFYASMDBKAJRKY-UHFFFAOYSA-N 0.000 description 2
- XAGORJMVDYHTNC-UHFFFAOYSA-N 1-methyl-2-(3,5,5-trimethylhexyl)cyclopentan-1-ol Chemical compound CC1(C(CCC1)CCC(CC(C)(C)C)C)O XAGORJMVDYHTNC-UHFFFAOYSA-N 0.000 description 2
- IENNKOXQSPDCEV-UHFFFAOYSA-N 1-methyl-2-phenylcyclopentan-1-ol Chemical group C1(=CC=CC=C1)C1C(CCC1)(O)C IENNKOXQSPDCEV-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 2
- MKOYLKTZDDFPFQ-UHFFFAOYSA-N 2-(3,4-dimethylpentyl)-1-ethylcyclopentan-1-ol Chemical group CC(CCC1C(CCC1)(O)CC)C(C)C MKOYLKTZDDFPFQ-UHFFFAOYSA-N 0.000 description 2
- GTBQJOXHPUWHFF-UHFFFAOYSA-N 2-(3,4-dimethylpentyl)-1-methylcyclopentan-1-ol Chemical group CC(CCC1C(CCC1)(O)C)C(C)C GTBQJOXHPUWHFF-UHFFFAOYSA-N 0.000 description 2
- OMEXMIOBTSIKHD-UHFFFAOYSA-N 2-heptyl-1-methylcyclopentan-1-ol Chemical group C(CCCCCC)C1C(CCC1)(O)C OMEXMIOBTSIKHD-UHFFFAOYSA-N 0.000 description 2
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 description 2
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000402754 Erythranthe moschata Species 0.000 description 2
- 244000153234 Hibiscus abelmoschus Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000233855 Orchidaceae Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MIZGSAALSYARKU-UHFFFAOYSA-N cashmeran Chemical compound CC1(C)C(C)C(C)(C)C2=C1C(=O)CCC2 MIZGSAALSYARKU-UHFFFAOYSA-N 0.000 description 2
- 229940043350 citral Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
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- 229920001971 elastomer Polymers 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- IOYHCQBYQJQBSK-UHFFFAOYSA-N orobol Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=C(O)C(O)=C1 IOYHCQBYQJQBSK-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 238000010419 pet care Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
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- KHQDWCKZXLWDNM-KPKJPENVSA-N (e)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound CC\C(CO)=C/CC1CC=C(C)C1(C)C KHQDWCKZXLWDNM-KPKJPENVSA-N 0.000 description 1
- CDEGOUYLXTUDAU-UHFFFAOYSA-N 1,1,2,3,3-pentamethyl-4,5,6,7-tetrahydro-2h-indene Chemical class CC1(C)C(C)C(C)(C)C2=C1CCCC2 CDEGOUYLXTUDAU-UHFFFAOYSA-N 0.000 description 1
- YNEQKUWRFVQFPF-UHFFFAOYSA-N 1,2,3-trimethylcyclopentene Chemical compound CC1CCC(C)=C1C YNEQKUWRFVQFPF-UHFFFAOYSA-N 0.000 description 1
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- HQWZJCUZXAPRHK-UHFFFAOYSA-N 1-ethenyl-2-(4-methylpentyl)cyclopentan-1-ol Chemical group CC(CCCC1C(CCC1)(O)C=C)C HQWZJCUZXAPRHK-UHFFFAOYSA-N 0.000 description 1
- FNKIECHOKBWKLN-UHFFFAOYSA-N 1-ethenyl-2-hexan-2-ylcyclopentan-1-ol Chemical group CC(CCCC)C1C(CCC1)(O)C=C FNKIECHOKBWKLN-UHFFFAOYSA-N 0.000 description 1
- VKHQILSQJXVMSB-UHFFFAOYSA-N 1-ethenyl-2-hexan-3-ylcyclopentan-1-ol Chemical group C(C)C(CCC)C1C(CCC1)(O)C=C VKHQILSQJXVMSB-UHFFFAOYSA-N 0.000 description 1
- XRJIRJAYXWQZDQ-UHFFFAOYSA-N 1-ethenyl-2-hexylcyclopentan-1-ol Chemical group C(CCCCC)C1C(CCC1)(O)C=C XRJIRJAYXWQZDQ-UHFFFAOYSA-N 0.000 description 1
- ZELZBJNGBRHIDW-UHFFFAOYSA-N 1-ethenyl-2-pentan-2-ylcyclopentan-1-ol Chemical group CC(CCC)C1C(CCC1)(O)C=C ZELZBJNGBRHIDW-UHFFFAOYSA-N 0.000 description 1
- FONFFFNIKLCIFF-UHFFFAOYSA-N 1-ethenyl-2-pentylcyclopentan-1-ol Chemical group C(CCCC)C1C(CCC1)(O)C=C FONFFFNIKLCIFF-UHFFFAOYSA-N 0.000 description 1
- AZIIKVDSYYLGCX-UHFFFAOYSA-N 1-ethenyl-2-propan-2-ylcyclopentan-1-ol Chemical group C(C)(C)C1C(CCC1)(O)C=C AZIIKVDSYYLGCX-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及新型环戊醇及其在改进、提高或改变香水、古龙水、花露水、织物护理产品、个人产品等的香气方面意想不到的有利用途。
Description
技术领域
本发明涉及新型化学实体和将其用作香料材料的方法。
背景技术
在香料行业当中,人们不断需要提供新的化学物质,使得香料生产商以及其他的人员能够制造用于香水、古龙水和个人护理产品的新的香料。该领域的技术人员能够理解,即使是化学结构中微小差异也会导致分子的气味、香调和特征的意想不到且显著的不同。这些变化使得香料生产商和其它人员得以将新的化合物用于制造新的香料。例如,取代基略微不同的苯化合物具有完全不同的气味概况[Ishikawa 等,International Journal ofQuantum Chemistry 79:101-108(2000)]。对于叔丁基环己烷,气味被认为取决于化合物构象,因此采取相同构象的类似物具有相似的气味。因此,许多反式化合物显示共有显著的尿-汗型气味,而相应的顺式化合物无气味的或者在多数情况下具有微弱且无法定义的花香或木材气味。然而,一些其他反式和顺式叔丁基环己烷显示具有相反的感官活性[Ohloff等,Helvetica Chimica Acta 66,Fasc.5:1343-1354(1983)]。因此,本领域技术人员难以预测某一给定的结构是否在感官活性中有效。鉴定理想的香料化学品持续造成巨大的挑战。
发明内容
本发明提供了新型化合物及其在改进、提高或改变香水、古龙水、花露水、织物护理产品、个人产品等的香气方面意想不到的有益应用。
本发明的一个实施方式涉及由下文所列式I表示的新型环戊醇:
其中R1代表C1-C2烃基;且其中R2代表C2-C9烃基。
本发明的另一个实施方式涉及由下文所列式II表示的新型环戊醇:
其中R3代表C1-C2烃基;且其中R4代表C3-C6烃基。
本发明的另一个实施方式涉及由下文所列式III表示的新型环戊醇:
其中R5选自乙基和乙烯基;R6代表C3-C6烃基。
本发明的另一个实施方式涉及一种通过添加嗅觉可接受量的上述新型化合物来改进、提高或改变香料制剂的方法。
本发明的另一个实施方式涉及包含上述新型化合物的香料组合物。
本发明的另一个实施方式涉及包含上述化合物的香料产品。
通过阅读以下说明书可以清楚地理解本发明的这些实施方式以及其他的实施方式。
具体实施方式
例如,通过以下实施例说明了本发明中由式I-III表示的新型环戊醇。
编号 | 化学名 |
结构1 | 1-乙基-2-丙基-环戊醇 |
结构2 | 1-乙基-2-异丙基-环戊醇 |
结构3 | 2-丁基-1-乙基-环戊醇 |
结构4 | 1-乙基-2-异丁基-环戊醇 |
结构5 | 2-仲丁基-1-乙基-环戊醇 |
结构6 | 1-乙基-2-戊基-环戊醇 |
结构7 | 1-乙基-2-(3-甲基-丁基)-环戊醇 |
结构8 | 1-乙基-2-(2-甲基-丁基)-环戊醇 |
结构9 | 1-乙基-2-(1-甲基-丁基)-环戊醇 |
结构10 | 2-(1,2-二甲基-丙基)-1-乙基-环戊醇 |
结构11 | 2-(2,2-二甲基-丙基)-1-乙基-环戊醇 |
结构12 | 2-乙基-二环戊基-2-醇 |
结构13 | 1-乙基-2-己基-环戊醇 |
结构14 | 1-乙基-2-(4-甲基-戊基)-环戊醇 |
结构15 | 1-乙基-2-(3-甲基-戊基)-环戊醇 |
结构16 | 1-乙基-2-(2-甲基-戊基)-环戊醇 |
结构17 | 1-乙基-2-(1-甲基-戊基)-环戊醇 |
结构18 | 2-(2,3-二甲基-丁基)-1-乙基-环戊醇 |
结构19 | 2-(1,3-二甲基-丁基)-1-乙基-环戊醇 |
结构20 | 2-(1,2-二甲基-丁基)-1-乙基-环戊醇 |
结构21 | 1-乙基-2-(2-乙基-丁基)-环戊醇 |
结构22 | 1-乙基-2-(1-乙基-丁基)-环戊醇 |
结构23 | 1-乙基-2-(1-乙基-2-甲基-丙基)-环戊醇 |
结构24 | 2-(3,3-二甲基-丁基)-1-乙基-环戊醇 |
结构25 | 2-(2,2-二甲基-丁基)-1-乙基-环戊醇 |
结构26 | 2-环己基-1-乙基-环戊醇 |
结构27 | 2-环戊基甲基-1-乙基-环戊醇 |
结构28 | 1-乙基-2-庚基-环戊醇 |
结构29 | 2-(3,4-二甲基-戊基)-1-乙基-环戊醇 |
结构30 | 2-丙基-1-乙烯基-环戊醇 |
结构31 | 2-异丙基-1-乙烯基-环戊醇 |
结构32 | 2-丁基-1-乙烯基-环戊醇 |
结构33 | 2-异丁基-1-乙烯基-环戊醇 |
结构34 | 2-仲丁基-1-乙烯基-环戊醇 |
结构35 | 2-戊基-1-乙烯基-环戊醇 |
结构36 | 2-(3-甲基-丁基)-1-乙烯基-环戊醇 |
结构37 | 2-(2-甲基-丁基)-1-乙烯基-环戊醇 |
结构38 | 2-(1-甲基-丁基)-1-乙烯基-环戊醇 |
结构39 | 2-(1,2-二甲基-丙基)-1-乙烯基-环戊醇 |
结构40 | 2-(2,2-二甲基-丙基)-1-乙烯基-环戊醇 |
结构41 | 2-乙烯基-二环戊基-2-醇 |
结构42 | 2-己基-1-乙烯基-环戊醇 |
结构43 | 2-(4-甲基-戊基)-1-乙烯基-环戊醇 |
结构44 | 2-(3-甲基-戊基)-1-乙烯基-环戊醇 |
结构45 | 2-(2-甲基-戊基)-1-乙烯基-环戊醇 |
结构46 | 2-(1-甲基-戊基)-1-乙烯基-环戊醇 |
结构47 | 2-(2,3-二甲基-丁基)-1-乙烯基-环戊醇 |
结构48 | 2-(1,3-二甲基-丁基)-1-乙烯基-环戊醇 |
结构49 | 2-(1,2-二甲基-丁基)-1-乙烯基-环戊醇 |
结构50 | 2-(2-乙基-丁基)-1-乙烯基-环戊醇 |
结构51 | 2-(1-乙基-丁基)-1-乙烯基-环戊醇 |
结构52 | 2-(1-乙基-2-甲基-丙基)-1-乙烯基-环戊醇 |
结构53 | 2-(3,3-二甲基-丁基)-1-乙烯基-环戊醇 |
结构54 | 2-(2,2-二甲基-丁基)-1-乙烯基-环戊醇 |
结构55 | 2-环己基-1-乙烯基-环戊醇 |
结构56 | 2-环戊基甲基-1-乙烯基-环戊醇 |
结构57 | 1-甲基-2-丙基-环戊醇 |
结构58 | 2-异丙基-1-甲基-环戊醇 |
结构59 | 2-丁基-1-甲基-环戊醇 |
结构60 | 2-异丁基-1-甲基-环戊醇 |
结构61 | 2-仲丁基-1-甲基-环戊醇 |
结构62 | 1-甲基-2-(2-甲基-烯丙基)-环戊醇 |
结构63 | 1-甲基-2-戊基-环戊醇 |
结构64 | 1-甲基-2-(3-甲基-丁基)-环戊醇 |
结构65 | 1-甲基-2-(2-甲基-丁基)-环戊醇 |
结构66 | 1-甲基-2-(1-甲基-丁基)-环戊醇 |
结构67 | 2-(1,2-二甲基-丙基)-1-甲基-环戊醇 |
结构68 | 2-(2,2-二甲基-丙基)-1-甲基-环戊醇 |
结构69 | 2-甲基-二环戊基-2-醇 |
结构70 | 2-己基-1-甲基-环戊醇 |
结构71 | 1-甲基-2-(4-甲基-戊基)-环戊醇 |
结构72 | 1-甲基-2-(3-甲基-戊基)-环戊醇 |
结构73 | 1-甲基-2-(2-甲基-戊基)-环戊醇 |
结构74 | 1-甲基-2-(1-甲基-戊基)-环戊醇 |
结构75 | 2-(2,3-二甲基-丁基)-1-甲基-环戊醇 |
结构76 | 2-(1,3-二甲基-丁基)-1-甲基-环戊醇 |
结构77 | 2-(1,2-二甲基-丁基)-1-甲基-环戊醇 |
结构78 | 2-(2-乙基-丁基)-1-甲基-环戊醇 |
结构79 | 2-(1-乙基-丁基)-1-甲基-环戊醇 |
结构80 | 2-(1-乙基-2-甲基-丙基)-1-甲基-环戊醇 |
结构81 | 2-(3,3-二甲基-丁基)-1-甲基-环戊醇 |
结构82 | 2-(2,2-二甲基-丁基)-1-甲基-环戊醇 |
结构83 | 2-环己基-1-甲基-环戊醇 |
结构84 | 2-环戊基甲基-1-甲基-环戊醇 |
结构85 | 2-庚基-1-甲基-环戊醇 |
结构86 | 2-(3,4-二甲基-戊基)-1-甲基-环戊醇 |
结构87 | 2-苯基-1-甲基-环戊醇 |
结构88 | 1-甲基-2-(3,5,5-三甲基-己基)-环戊醇 |
本发明的化合物可从环戊酮制备。反应步骤可以用以下方案表示:
其中R1和R2如上文所定义。
上述制备详述于实施例中。除非另有说明,材料购自艾尔德里奇化学公司(Aldrich Chemical Company)。
出乎意料地发现,本发明的化合物具有强烈且复杂的香料效果,例如新鲜、柑橘味和绿色植物的香调,并具有额外的木质气味以及樟脑和泥土底香 (undertone)。
本发明的化合物可以广泛地应用于目前的香料产品,包括香水和古龙水的制备,为个人护理产品(如肥皂、淋浴凝胶和护发产品)、织物护理产品、空气清新剂以及化妆用配制品加香。本发明还可以用于为清洁剂加香,所述清洁剂是例如但不限于洗涤剂、洗盘用材料、擦洗组合物、窗户清洁剂等。在这些制剂中,本发明的化合物可以单独使用,或者与其他的香味组合物、溶剂、佐剂等联用。可以使用的其它成分的性质和种类是本领域技术人员已知的。许多种类的香料可以用于本发明,仅有的限制是这些香料要能够与使用的其它组分相容。合适的香料包括但不限于水果香型,例如杏仁、苹果、樱桃、葡萄、梨、菠萝、桔子、草莓、覆盆子;麝香;花香,例如熏衣草型、玫瑰型、鸢尾型、康乃馨型。其它令人愉悦的香味包括草本植物香味以及源自松树、云杉和其它森林气味的林区香味。香料还可以源自各种油类,例如精油,或者源自植物材料,例如薄荷、留兰香等。
合适的香料的列表可参见美国专利第4,534,891号,其内容通过引用全文纳入本文。合适的香料的另一个来源可以参见W.A.Poucher在1959年编纂的Perfumes,Cosmetics and Soaps(《香料、化妆品和肥皂》)第二版。该专著中提供的香料包括刺槐、金合欢、素心兰、仙客来、蕨类植物、栀子、山楂、天芥菜、金银花、风信子、茉莉、紫丁香、百合、木兰、含羞草、水仙、刚切割的干草、橙花、兰花、木犀草、香豌豆、三叶草、晚香玉、香子兰、紫罗兰、桂竹香等。
本发明的化合物可以与互补香料化合物联用。本文所用术语“互补香料化合物”定义为选自下组的香料化合物:2-[(4-甲基苯基)亚甲基]-庚醛(阿卡丽尔醛 (Acalea))、异戊基氧基乙酸烯丙酯(格蓬酯(Allyl Amyl Glycolate))、丙烷-1,3-二酸 (3,3-二甲基环己基)乙基乙基酯(麝香果酯(Applelide))、(E/Z)-1-乙氧基-1-癸烯(阿可替克(Arctical))、2-乙基-4-(2,2,3-三甲基-3-环-戊烯-1-基)-2-丁烯-1-醇(白檀醇(Bacdanol))、2-甲基-3-[(1,7,7-三甲基二环[2.2.1]庚-2-基)氧基]外-1-丙醇(伯纳菲(Bornafix))、1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚-4-酮(开司米酮(Cashmeran))、三甲基环戊烯基甲基氧杂二环辛烷(黑醋栗环醚(Cassiffix))、1,1-二甲氧基-3,7-二甲基-2,6-辛二烯(柠檬醛DMA(Citral DMA))、3,7-二甲基-6-辛烯-1-醇(香茅醇(Citronellol))、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基乙酸酯(乙酸三环癸烯酯(Cyclacet))、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基丙酸酯(丙酸三环癸烯酯(Cyclaprop))、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1G-茚-5/6-基丁酸酯(正丁酸三环癸烯酯(Cyclobutanate))、1-(2,6,6-三甲基-3-环己烯-1-基)-2-丁烯-1-酮(δ-突厥酮(Delta Damascone))、3-(4-乙基苯基)-2,2-二甲基丙腈(鲜花腈(Fleuranil))、3-(O/P-乙基苯基)2,2-二甲基丙醛(海风醛(Floralozone))、四氢-4-甲基-2-(2-甲基丙基)-2H-吡喃-4-醇(铃兰醚(Floriffol))、1,3,4,6,7,8-六氢-4,6,6,7,8,8-六甲基环戊--2-苯并吡喃(佳乐麝香(Galaxolide))、1-(5,5-二甲基-1-环己烯-1-基)戊-4-烯-1-酮(格蓬酮(Galbascone))、E/Z-3,7-二甲基-2,6-辛二烯-1-基乙酸酯(乙酸香叶酯(GeranylAcetate))、á-甲基-1,3-苯并间二氧杂环戊烯基-5-丙醛(新洋茉莉醛(Helional))、 1-(2,6,6-三甲基-2-环己烯-1-基)-1,6-庚二烯-3-酮(新罗酮(Hexalon))、(Z)-3-己烯基-2- 羟基苯甲酸酯(水杨酸己烯酯(Hexenyl Salicylate,CIS-3))、4-(2,6,6-三甲基-2-环己烯 -1-基)-3-丁烯-2-酮(α紫罗兰酮(Iononeα))、1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2- 萘基)-乙烷-1-酮(龙涎酮(Iso E Super))、3-氧杂-2-戊基环戊烷乙酸甲酯(高顺式二氢茉莉酮酸甲酯(Kharismal))、2,2,4-三甲基-4-苯基-丁腈(圆柚腈(Khusinil))、3,4,5,6,6- 五甲基庚-3-烯-2-酮(高芳烯(Koavone))、3/4-(4-羟基-4-甲基-戊基)环己烯-1-甲醛(新铃兰醛(Lyral))、3-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(γ甲基紫罗兰酮(Methyl Iononeγ))、1-(2,6,6-三甲基-2-环己烯-1-基)戊-1-烯-3-酮(特级α甲基紫罗兰酮(Methyl IononeαExtra)、正常甲基紫罗兰酮(Methyl Ionone N))、3-甲基-4-苯基丁烷-2-醇(缪格斯亚(Muguesia))、环十五碳-4-烯-1-酮(麝香Z4(Musk Z4))、 3,3,4,5,5-五甲基-11,13-二氧杂三环[7.4.0.0<2,6>]十三碳-2(6)-烯(内布罗恩 (Nebulone))、3,7-二甲基-2,6-辛二烯-1-基乙酸酯(醋酸橙花酯(Neryl Acetate))、3,7- 二甲基-1,3,6-辛三烯(罗勒烯(Ocimene))、邻-甲苯基乙醇(邻甲苯基乙醇(Peomosa))、 3-甲基-5-苯基戊醇(苯乐戊醇(Phenoxanol))、1-甲基-4-(4-甲基-3-戊烯基)环己-3-烯 -1-甲醛(环海风醛(Precyclemone B))、4-甲基-8-亚甲基-2-金刚烷醇(普利斯曼醇 (Prismantol))、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(圣檀醇 (Sanjinol))、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(檀香醇(Santaliff))、松油醇(Terpineol)、2,4-二甲基-3-环己烯-1-甲醛(女贞醛(Triplal))、十氢-2,6,6,7,8,8- 六甲基-2H-茚并[4,5-B]呋喃(超级龙涎香醚(Trisamber))、2-叔丁基环己基乙酸酯(乙酸邻叔丁基环己酯(Verdox))、4-叔丁基环己基乙酸酯(鸢尾酯(Vertenex))、乙酰基柏木烯(甲基柏木酮(Vertofix))、3,6/4,6-二甲基环己-3-烯-1-甲醛(艾薇醛(Vertoliff))和 (3Z)-1-[(2-甲基-2-丙烯基)氧基]-3-己烯(绿花酯(Vivaldie))。
气味香调的复杂度是指存在多种和/或混合的但已有定义的气味而不是单一香调或一些简单可识别的香调。高级别的复杂度也被分配给具有由于直接贡献或产生的许多气味的嗅觉组合导致的模糊的且某些程度上难以定义香调的化合物。高级别复杂度的香料材料被认为具有不同寻常的高质量。
术语“香料制剂”、“香料组合物”和“香味组合物”意思相同,表示一种消费品组合物,它是包括例如醇类、醛类、酮类、酯类、醚类、内酯类、腈类、天然油类、合成油类和硫醇类的化合物的混合物,这些化合物混合在一起使得单独组分的组合气味产生令人愉悦或希望的香味。本发明的香料制剂是一种包含本发明化合物的消费品组合物。本发明的香料制剂可包含本发明的化合物并且还包含上述互补香料化合物。
术语“香料产品”表示包含增加芳香或掩饰恶臭的香料成分的消费品。香料产品可包括,例如,香水、古龙水、肥皂、液体皂、沐浴凝胶、泡沫浴、化妆品、皮肤护理产品(如面霜、乳液和剃须产品)、用于洗发、冲洗、护理、漂白、着色、染色和定型的头发护理产品、除臭剂和止汗剂、女性护理产品(如卫生棉条和妇女卫生巾)、婴儿护理产品(如尿布、围兜和湿巾)、家庭护理用品(如浴巾纸、面巾纸、纸手帕或纸巾)、织物产品(如织物柔软剂和清新剂)、空气护理产品(如空气清新剂和香料递送体系)、化妆品制剂、清洁剂和消毒剂(如洗涤剂、洗盘用材料、擦洗组合物)、玻璃和金属清洁剂(如窗户清洁剂、工作台面清洁剂、地板和地毯清洁剂、厕所清洁剂和漂白添加剂),清洗剂(如各种用途、重型和洗手或精细织物清洗剂,包括衣物洗涤剂和漂洗添加剂)、牙齿和口腔卫生产品(如牙膏、牙凝胶、牙线、假牙清洁剂、假牙粘合剂、牙粉、牙齿美白和漱口水)、保健和营养产品及食品(如零食和饮料产品)。本发明的香料产品是一种包含本发明化合物的消费品。本发明的香料产品可包含本发明的化合物并且还包含上述互补香料化合物。
短语“改进、提高或改变香料制剂”中的术语“改进”应理解为将所述香料制剂提升至更理想的特性。术语“提高”应理解为使得所述香料制剂的效果更强,或者向所述香料制剂提供改进的特性。术语“改变”应理解为向所述香料制剂提供改变的特性。
术语“嗅觉可接受的量”应理解为表示香料制剂中化合物的量,在该量下,所述化合物能够贡献其独特的嗅觉特性。但是,所述香料制剂的嗅觉效果是每种香料成分的效果的总和。因此,可以使用本发明的化合物来改进或提高所述香料制剂的芳香特性,或者通过改变制剂中的其它成分贡献的嗅觉反应而改变其芳香特性。嗅觉可接受的量将根据许多的因素变化,这些因素包括其它成分、它们的相对含量、以及所需的嗅觉效果。
在香料制剂中使用的本发明化合物的量为约0.005至约70重量%,优选0.05 至约50重量%,更优选约0.5至约25重量%,更优选约1至约10重量%。本领域技术人员能使用所需的量来得到理想的香料效果和强度。除了本发明的化合物之外,其它材料也可以与所述香料制剂一起使用,从而包封和/或递送香料。一些熟知的材料是例如(但不限于)聚合物、低聚物、其它非聚合物(如表面活性剂、乳化剂、脂质(包括脂肪)、蜡和磷脂)、有机油、矿物油、石油、天然油类、香味固定剂、纤维、淀粉、糖和固体表面材料(如沸石和二氧化硅)。
在香料制剂中使用时,这些组分提供其它的香调,使得香料制剂更宜人且更引人注意,并增加感知价值。这些材料中发现的气味特性都有助于美化并提高最终的香韵(accord)和改善香料中其它材料的性能。
此外,还意外地发现,本发明的化合物提供了优越的成分性能并且在消解恶臭的应用(如身体排汗、环境气味(如霉菌和发霉)、浴室等)中具有出乎意料的优点。本发明的化合物基本上消除了对恶臭的感觉和/或防止此类恶臭的形成,因此可与大量功能性产品一起使用。
本文中提供了所述功能性产品的示例以便说明本发明的各个方面。然而,它们并不旨在限制本发明的范围。所述功能性产品可以包括例如常规房间清新剂(或除臭剂)组合物,如房间清新剂喷雾剂、气雾剂或其他喷雾剂;香味漫射体,吸液芯或其他液体系统或固体,如在香盒和塑料内的蜡烛或蜡基,小香囊中的粉剂或干喷雾剂或固体胶棒形式的凝胶剂;通过洗衣机应用施加的衣物除臭剂,如去污剂、粉末、液体、增白剂或织物柔软剂中的衣物除臭剂;织物清新剂、亚麻布喷雾剂、壁橱块体、壁橱气溶胶喷雾剂,或衣物储存区内或干洗中为克服衣物上残留的溶剂味使用的产品;浴室附属品,如纸巾、草纸、卫生巾、小毛巾、一次性毛巾、一次性尿布、尿布桶除臭剂;清洁剂,如消毒剂和马桶清洁剂;化妆品,如止汗药和除臭剂,粉末、气溶胶、液体或固体形式的普通去体臭药;或护发产品,如喷发剂、调理剂、柔顺剂、头发颜料和染料、永久性卷发剂、脱毛剂、直发剂、头发整饰应用(如润发脂、乳膏和洗涤剂);加有药品的护发产品,它们含有诸如二硫化硒、煤焦油或水杨酸盐之类的成分;或洗发剂;或足部护理产品,如修面和使用润肤露之后使用的足部药粉、液体或古龙水;或肥皂和合成去污剂,如条、液体、起泡剂或粉末;气味控制,如制造过程中的气味控制,如在织物整理工业和印刷工业(墨水和纸)中;废水和废气控制,如制浆、原料场和肉类加工中涉及的过程、污水处理、垃圾袋或垃圾处理中的废水和废气控制;或产品气味控制,如纺织制成品、橡胶制成品或汽车香片中的产品气味控制;农业和宠物护理产品,如狗和母鸡家庭污水和家禽与宠物护理产品(如除臭剂、洗发剂或清洁剂),或动物垃圾材料;以及在大规模封闭空气系统(如大会堂、地铁和运输系统)中使用的产品。
因此可见,本发明的组合物通常是所述恶臭冲消剂与载体在一起,所述恶臭冲消剂可通过或从所述载体导入存在恶臭的大气空间中或沉积恶臭的基质上。例如,所述载体可以是气溶胶喷射剂诸如氯氟-甲烷,或是固体诸如蜡、塑料材料、橡胶、惰性粉末或凝胶。在吸液芯型空气清新剂中,所述载体是基本上无气味的低挥发性的液体。在若干应用中,本发明的组合物含有表面活性剂或消毒剂,而在其他应用中,所述恶臭冲消剂存在于纤维质基质上。在本发明的许多组合物中,还存在赋予所述组合物香气的香料组分。上述香料均可使用。
恶臭冲消有效量应理解为表示在功能性产品中采用的本发明的恶臭冲消剂在器官感觉上有效地削弱给定的恶臭、同时减小所述气味水平的综合强度的量,其中所述给定的恶臭存在于大气空间中或沉积在基质上。所采用的恶臭冲消剂的确切量可以根据恶臭冲消剂的类型、采用的载体的类型和所需的恶臭冲消的程度而变化。一般而言,恶臭冲消剂的存在量是获得所需结果需要的普通剂量。该剂量是本领域技术人员已知的。在一个优选实施方式中,当与恶臭的固体或液体功能性产品(例如肥皂和去污剂)联合使用时,本发明的组合物的存在量可以是约0.005至约50 重量%、优选地约0.01至约20重量%、且更优选为约0.05至约5重量%,当与恶臭的气体功能性产品联合使用时,本发明的组合物的存在量可以是每立方米空气约 0.1至10mg。
下面提供了本发明的具体实施方式。本发明的其它改进对于本领域的技术人员来说将是显而易见的。应当理解,这些改进包括在本发明范围之内。除非另有说明,所有的百分数都是重量百分数,ppm表示百万分之一份,L表示升,mL表示毫升,g表示克,mol表示摩尔,psi表示磅力每平方英寸,且mmHg表示毫米(mm) 汞柱(Hg)。实施例中使用的IFF应理解为美国纽约州纽约市的国际香料和香精公司(International Flavors&FragrancesInc.)。
实施例1
2-戊基-环戊酮的制备:向3-L反应烧瓶中加入环戊酮(500g,6mol)、水 (H2O)(500mL)和氢氧化钠(NaOH)(10g,0.25mol)。在3小时内向反应烧瓶中添加戊醛(430g,5mol),同时将温度维持在25-30℃。添加完成后,将反应老化2小时并使用盐酸(HCl)(30g,0.3mol)中和,同时将温度维持在25-30℃。将该反应物另外老化2小时。分离有机层并使用饱和碳酸氢钠(NaHCO3)水溶液(200mL) 清洗。对获得的粗产物分馏以提供2-亚戊基环戊酮(523g),在3mmHg下其沸点为122℃。向1-L密闭式高压釜中加入2-亚戊基环戊酮(523g)和钯碳(Pd/C)(2 g)。使用氮气对高压釜吹扫三次,随后使用氢气吹扫三次。随后将高压釜搅拌器打开至1500rpm并将压力设置为100psi。使反应放热至约120℃并在该温度下维持2小时。将高压釜冷却至室温。随后排出氢气并随后使用氮气对高压釜吹扫三次。通过过滤以除去Pd/C。获得粗产物2-戊基-环戊酮(520g)并在未进行进一步纯化的情况下用于以下步骤中。
2-亚戊基-环戊酮:
1H NMR(500MHz,CDCl3):6.40ppm(t,1H),3.75-3.15ppm(m,2H),2.70-2.55 ppm(m,2H),2.25-2.15ppm(m,1H),1.96-2.14ppm(m,1H),1.71-1.82ppm(m,2H), 1.48-1.57ppm(m,1H),1.20-1.37ppm(m,3H),0.88ppm(t,3H,J=6.95Hz)
2-戊基-环戊酮:
1H NMR(500MHz,CDCl3):2.25-2.32ppm(m,1H),2.18-2.25ppm(m,1H), 1.96-2.14ppm(m,3H),1.71-1.82ppm(m,2H),1.48-1.57ppm(m,1H),1.20-1.37ppm (m,7H),0.88ppm(t,3H,J=6.95Hz)
实施例2
1-甲基-2-戊基-环戊醇(结构63)的制备:向3-L反应烧瓶中加入含甲基氯化镁(MeMgCl)的四氢呋喃(THF)(800mL,2.4mol)溶液和THF(500mL)。将反应烧瓶冷却至5-10℃。在1小时内向反应混合物中添加2-戊基-环戊酮(370g,2.4mol) (如上文实施例1中所述制备)。将反应老化4小时,随后使用乙酸(CH3COOH) (160g)中和,同时将温度维持在5-10℃。将反应混合物倒入水(3L)和甲苯(1L) 中。分离有机层并分级蒸馏以提供1-甲基-2-戊基-环戊醇(245g),在3mmHg下其沸点为150-152℃。
1H NMR(500MHz,CDCl3):1.85-1.91ppm(m,1H),1.62-1.76ppm(m,3H), 1.17-1.59ppm(m,10H),1.27ppm(s,3H),1.10-1.20ppm(m,2H),0.89ppm(t,3H,J= 6.85Hz)
实施例3
用类似方法制备以下环戊醇。
1-乙基-2-异丁基-环戊醇(结构4)(5mmHg下沸点为145-150℃)
1H NMR(500MHz,CDCl3):1.82-1.90ppm(m,1H),1.62-1.81ppm(m,4H), 1.48-1.61ppm(m,3H),1.34-1.47ppm(m,2H),1.12-1.25ppm(m,2H),1.04ppm(s, 1H),0.94ppm(t,3H,J=7.65Hz),0.93ppm(d,3H,J=6.60Hz),0.86ppm(d,3H,J= 6.55Hz)
1-乙基-2-戊基-环戊醇(结构6)(3mmHg下沸点为165-166℃)
1H NMR(500MHz,CDCl3):1.84-1.90ppm(m,1H),1.60-1.78ppm(m,4H), 1.35-1.58ppm(m,6H),1.15-1.35ppm(m,6H),1.13ppm(s,1H),0.94ppm(t,3H,J= 7.5Hz),0.89ppm(t,3H,J=6.7Hz)
1-乙基-2-(3-甲基-丁基)-环戊醇(结构7)(5mmHg下沸点为155-159℃)
1H NMR(500MHz,CDCl3):1.84-1.90ppm(m,1H),1.66-1.81ppm(m,2H),1.64 ppm(t,2H,J=7.45Hz),1.45-1.59ppm(m,2H),1.35-1.45ppm(m,4H),1.18-1.28 ppm(m,1H),1.121.18ppm(m,2H),1.05ppm(s,1H),0.94ppm(t.3H,J=7.50Hz), 0.89ppm(d,3H,J=6.25Hz),0.88ppm(d,3H,J=6.15Hz)
2-乙基-二环戊基-2-醇(结构12)(5mmHg下沸点为135-140℃)
1HNMR(500MHz,CDCl3):1.87-1.91ppm(m,1H),1.42-1.84ppm(m,15H), 1.11-1.20ppm(m,2H),1.10ppm(s,1H),0.94ppm(t.3H,J=7.45Hz)
1-乙基-2-庚基-环戊醇(结构28)(3mmHg下沸点为176-178℃)
1H NMR(500MHz,CDCl3):1.84-1.98ppm(m,1H),1.61-1.78ppm(m,4H), 1.35-1.60ppm(m,6H),1.12-1.34ppm(m,10H),0.92-1.06ppm(m,4H),0.88ppm(t. 3H,J=6.53Hz)
2-(3,4-二甲基-戊基)-1-乙基-环戊醇(结构29)(3mmHg下沸点为163-166° C)
1H NMR(500MHz,CDCl3):1.84-1.94ppm(m,1H),1.66-1.78ppm(m,2H), 1.62-1.66ppm(m,2H),1.47-1.62ppm(m,3H),1.35-1.46ppm(m,3H),1.23-1.31ppm (m,2H),1.11-1.22ppm(m,1H),1.02-1.09ppm(m,2H),0.94ppm(t,3H,J=7.53Hz), 0.86ppm(d,3H,J=6.83Hz,of d,J=1.53Hz),0.78-0.82ppm(m,6H)
2-异丁基-1-乙烯基-环戊醇(结构33)(5mmHg下沸点为130-132℃)
1H NMR(500MHz,CDCl3):5.86ppm(d,1H,J=17.25Hz,of d,J=10.72Hz), 5.26ppm(d,1H,J=17.27Hz,of d,J=1.42Hz),5.10ppm(d,1H,J=10.72Hz,of d,J =1.40Hz),1.44-1.96ppm(m,8H),1.19ppm(s,1H),1.09-1.18ppm(m,2H),0.90ppm (d,3H,J=6.60Hz),0.84ppm(d,3H,J=6.56Hz)
2-(3-甲基-丁基)-1-乙烯基-环戊醇(结构36)(3mmHg下沸点为125-128℃)
1H NMR(500MHz,CDCl3):5.87ppm(d,1H,J=17.26Hz,of d,J=10.75Hz), 5.27ppm(d,1H,J=17.28Hz,of d,J=1.23Hz),5.09ppm(d,1H,J=10.73Hz,of d,J =1.18Hz),1.89-1.96ppm(m,1H),1.74-1.88ppm(m,2H),1.56-1.72ppm(m,3H), 1.44-1.54ppm(m,2H),1.37-1.43ppm(m,1H),1.29ppm(s,1H),1.06-1.24ppm(m, 3H),0.87ppm(d,3H,J=6.45Hz),0.86ppm(d,3H,J=6.40Hz)
2-乙烯基-二环戊基-2-醇(结构41)(3mmHg下沸点为130℃)
1H NMR(500MHz,CDCl3):5.95ppm(d,1H,J=17.23Hz,of d,J=10.71Hz), 5.27ppm(d,1H,J=17.27Hz,of d,J=1.42Hz),5.02ppm(d,1H,J=10.72Hz,of d,J =1.40Hz),1.70-1.91ppm(m,6H),1.41-1.69ppm(m,8H),1.39ppm(s,1H),0.98-1.21 ppm(m,2H)
2-异丁基-1-甲基-环戊醇(结构60)(5mmHg下沸点为125-130℃)
1H NMR(500MHz,CDCl3):1.83-1.90ppm(m,1H),1.49-1.80ppm(m,6H), 1.35-1.43ppm(m,1H),1.26ppm(s,3H),1.18-1.24ppm(m,2H),1.14ppm(s,1H), 0.93ppm(d.3H,J=6.65Hz),0.86ppm(d,3H,J=6.55Hz)
1-甲基-2-(2-甲基-烯丙基)-环戊醇(结构62)(25mmHg下沸点为122-125° C)
1H NMR(500MHz,CDCl3):1.84-2.26ppm(m,2H),1.48-1.81ppm(m,6H), 1.38-1.47ppm(m,2H),1.37ppm(s,1H),1.27ppm(d,3H,J=1.48Hz),1.15-1.35ppm (m,1H),1.14ppm(s,51H),0.96-1.12ppm(m,1H),0.86ppm(d,3H,J=6.84Hz), 0.81ppm(d,3H,J=6.68Hz),0.79ppm(d,3H,J=6.80Hz)
1-甲基-2-(3-甲基-丁基)-环戊醇(结构64)(5mmHg下沸点为145-149℃)
1H NMR(500MHz,CDCl3):1.84-1.91ppm(m,1H),1.62-1.79ppm(m,3H), 1.44-1.61ppm(m,3H),1.32-1.43ppm(m,2H),1.27ppm(s,3H),1.11-1.25ppm(m, 4H),0.90ppm(d.3H,J=6.45Hz),0.88ppm(d,3H,J=6.35Hz)
2-甲基-二环戊基-2-醇(结构69)(5mmHg下沸点为125-128℃)
1H NMR(500MHz,CDCl3):1.90-1.96ppm(m,1H),1.73-1.84ppm(m,3H), 1.67-1.72ppm(m,3H),1.42-1.67ppm(m,6H),1.37-1.41ppm(m,1H),1.34ppm(s, 3H),1.30ppm(s,1H),1.10-1.21ppm(m,2H)
1-甲基-2-(2-甲基-戊基)-环戊醇(结构73)(3mmHg下沸点为105-107℃)
1H NMR(500MHz,CDCl3):1.00-2.35ppm(m,15H),1.25ppm(s,3H),0.89ppm (t,3H,J=6.75Hz),0.84ppm(d,3H,J=6.60Hz)
2-庚基-1-甲基-环戊醇(结构85)(3mmHg下沸点为175-178℃)
1H NMR(500MHz,CDCl3):1.84-2.32ppm(m,2H),1.61-1.82ppm(m,3H), 1.13-1.58ppm(m,18H),0.88ppm(t,3H,J=6.60Hz)
2-(3,4-二甲基-戊基)-1-甲基-环戊醇(结构86)(5mmHg下沸点为155-158° C)
1H NMR(500MHz,CDCl3):4.72ppm(s,2H),2.24ppm(d,1H,J=13.86Hz,of d,J=4.10Hz),1.95ppm(d,1H,J=13.76Hz,of d,J=10.15Hz),1.75-1.86ppm(m, 1H),1.67-1.74ppm(m,7H),1.52-1.62ppm(m,1H),1.40-1.46ppm(m,1H),1.30ppm (s,3H),1.13ppm(s.1H)
2-苯基-1-甲基-环戊醇(结构87)(5mmHg下沸点为125-130℃)
1H NMR(500MHz,CDCl3):7.15-7.30ppm(m,5H),2.86-2.92ppm(d,1H,J= 13.36Hz,of d,J 10=4.07Hz),2.45-2.52ppm(d,1H,J=13.32Hz,of d,J=10.41Hz), 1.93-2.45ppm(m,1H),1.61-1.85ppm(m,4H),1.48-1.53ppm(m,2H),1.32ppm(s, 3H),1.13ppm(s,1H)
1-甲基-2-(3,5,5-三甲基-己基)-环戊醇(结构88)(5mmHg下沸点为160-162 ℃)
1H NMR(500MHz,CDCl3):1.81-2.17ppm(m,2H),1.63-1.78ppm(m,3H), 1.34-1.55ppm(m,5H),1.27ppm(2s,3H),1.10-1.26ppm(m,3H),0.99-1.10ppm(m, 2H),0.88-0.95ppm(m,12H)
实施例4
上述环戊醇的香味特性用以下方法评价:(i)0至10的气味强度,其中0=无, 1=非常弱,5=中度,10=极强;和(ii)复杂度级别,其中0=无,1=非常低, 5=中度,10=极高。平均评分如下所示:
在所有评估的结构中,结构6、7、63和64表现出特别希望的、强烈的和复杂的气味。它们的有利性质是意想不到的。
实施例5
此外,通过对来自上述示意图(参见第7页)的相应取代的α环亚戊基或2- 取代的环戊酮的氢化,制备了许多环戊醇类似物。
2-异丁基-环戊醇(结构89)
1H NMR(500MHz,CDCl3):3.75-4.14ppm(m,1H),0.82-1.84ppm(m,17H)
2-戊基-环戊醇(结构90)
1H NMR(500MHz,CDCl3):3.75-4.14ppm(m,1H),1.35-1.80ppm(m,16H), 0.89ppm(t,3H,J=6.79Hz)
二环戊基-2-醇(结构91)
1H NMR(500MHz,CDCl3):3.75-4.14ppm(m,1H),2.05-2.20(m,2H),1.45-1.75 ppm(m,15H)
2-庚基-环戊醇(结构92)
1H NMR(500MHz,CDCl3):3.75-4.14ppm(m,1H),1.10-1.80ppm(m,20H),0.87 ppm(t,3H,J-6.79Hz)
2-苯基-环戊醇(结构93)
1H NMR(500MHz,CDCl3):7.00-7.25ppm(m,5H),3.75-4.14ppm(m,1H), 2.10-2.60ppm(m,3H),1.50-1.80ppm(m,7H)
2-辛基-环戊醇(结构94)
1H NMR(500MHz,CDCl3):3.75-4.14ppm(m,1H),1.10-1.80ppm(m,22H),0.87 ppm(t,3H,J-6.79Hz)
2-(1-乙烯基-己-5-烯基)-环戊醇(结构95)
1H NMR(500MHz,CDCl3):5.60-5.79ppm(m,2H),4.80-5.05ppm(m,4H), 3.75-4.14ppm(m,1H),1.35-2.20ppm(m,15H)
2-(5,6-二甲基-环己-3-烯基)-环戊醇(结构96)
1H NMR(500MHz,CDCl3):5.35-5.60ppm(m,2H),3.75-4.14ppm(m,1H), 1.45-2.25ppm(m,13H),0.80-0.95ppm(m,6H)
2-(2-苯基-丙基)-环戊醇(结构97)
1H NMR(500MHz,CDCl3):7.05-7.25ppm(m,5H),3.75-4.14ppm(m,1H), 2.80-3.10ppm(m,1H),1.50-2.00ppm(m,10H),1.29ppm(d,3H,J=6.75Hz)
2-((E)-3,7-二甲基-辛-2,6-二烯基)-环戊醇(结构98)
1H NMR(500MHz,CDCl3):5.15-5.25ppm(m,2H),3.75-4.14ppm(m,1H), 1.20-2.25ppm(m,23H)
2-(1,5-二甲基-1-乙烯基-己-4-烯基)-环戊醇(结构99)
1H NMR(500MHz,CDCl3):5.70-5.80ppm(m,1H),4.90-5.15ppm(m,3H), 3.75-4.14ppm(m,1H),1.25-1.90ppm(m,18H),1.04ppm(s,3H)
2-[2-(2,2,3-三甲基-环戊基)-乙基]-环戊醇(结构100)
1H NMR(500MHz,CDCl3):3.75-4.14ppm(m,1H),1.61-1.84ppm(m,6H), 1.31-1.59ppm(m,7H),1.02-1.24ppm(m,5H),0.72-0.92ppm(m,6H),0.50ppm(s, 3H)
2-(2,2,6-三甲基-环己基甲基)-环戊醇(结构101)
1H NMR(500MHz,CDCl3):3.77-4.14ppm(m,1H),0.98-2.01ppm(m,18H), 0.74-0.98ppm(m,9H)
2-(4-异丙基-苯基)-环戊醇(结构102)
1H NMR(500MHz,CDCl3):7.09-7.20ppm(m,4H),3.77-4.14ppm(m,1H), 2.48-2.88ppm(m,3H),1.65-2.15ppm(m,8H),1.24ppm(d,6H,J=7.03Hz)
2-(4-叔丁基-苯基)-环戊醇(结构103)
1H NMR(500MHz,CDCl3):7.27-7.37ppm(m,2H),7.12-7.17ppm(m,2H), 3.77-4.14ppm(m,1H),2.48-2.86(m,2H),1.20-2.08ppm(m,8H),1.31ppm(s,9H)
1-环丙基-2-戊基-环戊醇(结构104)
1H NMR(500MHz,CDCl3):1.08-2.03(m,15H),1.02(br.S.,1H),0.77-0.97(m, 4H),0.28-0.50(m,3H),0.17-0.27(m,1H)
实施例6
也评估了上述环戊醇类似物(即结构89-104)的香味特性。气味概况如下所示:
上述实施例中环戊醇和环戊醇类似物的评估令人吃惊地显示,实施例4的1- 取代的环戊醇(其中所述取代是C1-C2烃基)具有希望的、强烈的和复杂的气味,这在实施例6的环戊醇类似物中没有观察到。因此,1-取代的环戊醇的这类有利特性是出乎意料的和具有优势的。
Claims (23)
1.一种通过添加嗅觉可接受量的化合物来改进、提高或改变香料制剂的方法,所述化合物选自:1-乙基-2-戊基-环戊醇、1-乙基-2-(3-甲基-丁基)-环戊醇、1-甲基-2-戊基-环戊醇和1-甲基-2-(3-甲基-丁基)-环戊醇。
2.如权利要求1所述的方法,所述嗅觉可接受量是所述香料制剂的0.005至50重量%。
3.如权利要求1所述的方法,所述嗅觉可接受量是所述香料制剂的0.5至25重量%。
4.如权利要求1所述的方法,所述嗅觉可接受量是所述香料制剂的1至10重量%。
5.一种香料制剂,其包含嗅觉可接受量的选自1-乙基-2-戊基-环戊醇、1-乙基-2-(3-甲基-丁基)-环戊醇、1-甲基-2-戊基-环戊醇和1-甲基-2-(3-甲基-丁基)-环戊醇的化合物。
6.如权利要求5所述的香料制剂,所述嗅觉可接受量是所述香料制剂的0.005至50重量%。
7.如权利要求5所述的香料制剂,所述嗅觉可接受量是所述香料制剂的0.5至25重量%。
8.如权利要求5所述的香料制剂,所述嗅觉可接受量是所述香料制剂的1至10重量%。
9.如权利要求5所述的香料制剂,所述香料制剂还包含选自聚合物和非聚合物的材料。
10.如权利要求9所述的香料制剂,所述材料选自:表面活性剂、脂肪、蜡、磷脂、有机油、矿物油、石油、香味固定剂、纤维、淀粉、糖、沸石和二氧化硅。
11.如权利要求10所述的香料制剂,所述表面活性剂是乳化剂。
12.如权利要求10所述的香料制剂,所述有机油是天然油。
13.一种化合物,其选自:1-乙基-2-戊基-环戊醇、1-乙基-2-(3-甲基-丁基)-环戊醇、1-甲基-2-戊基-环戊醇和1-甲基-2-(3-甲基-丁基)-环戊醇。
14.一种包含嗅觉可接受量的如权利要求13所述化合物的香料产品。
15.如权利要求14所述的香料产品,所述香料产品选自:香水、化妆品,个人护理产品、织物护理产品、家庭护理用品及食品。
16.如权利要求14所述的香料产品,所述香料产品是香料递送体系。
17.如权利要求14所述的香料产品,所述香料产品选自女性护理产品、婴儿护理产品。
18.如权利要求14所述的香料产品,所述香料产品选自皮肤护理产品、头发护理产品、空气护理产品及牙齿和口腔卫生产品。
19.如权利要求14所述的香料产品,所述香料产品是清洁剂。
20.如权利要求14所述的香料产品,所述香料产品是清洗剂。
21.如权利要求14所述的香料产品,所述香料产品是消毒剂。
22.如权利要求14所述的香料产品,所述香料产品是除臭剂。
23.如权利要求14所述的香料产品,所述香料产品选自古龙水、花露水、肥皂、沐浴凝胶,泡沫浴、止汗剂、空气清新剂、保健和营养产品。
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US14/103,100 US9290718B2 (en) | 2013-12-11 | 2013-12-11 | Cyclopentanol compounds |
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US3852219A (en) * | 1970-11-10 | 1974-12-03 | Givaudan Corp | Odorant compositions including 2-butyl -1-alkynylcycloalkan-1-ols and derivatives thereof |
US4719043A (en) * | 1986-03-21 | 1988-01-12 | Henkel Kommanditgesellschaft Auf Aktien | Isomeric 1-alkyl/alkenyl-2,2,4(2,4,4)-trimethyl cyclopentan-1-ols as perfumes |
CN101918345A (zh) * | 2008-01-22 | 2010-12-15 | 弗门尼舍有限公司 | 赋予树液和/或泥土类型香调的加香成分 |
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US3769330A (en) * | 1970-11-10 | 1973-10-30 | Givaudan Corp | 2-butyl-1-alkynyl-cycloalkan-1-ols and derivatives thereof |
US4534891A (en) | 1982-11-12 | 1985-08-13 | International Flavors & Fragrances Inc. | Branched C13 -alk-1-en-5-ones and use thereof in perfumery |
WO2011073843A1 (en) * | 2009-12-17 | 2011-06-23 | Firmenich Sa | Odorant alcohols |
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US3852219A (en) * | 1970-11-10 | 1974-12-03 | Givaudan Corp | Odorant compositions including 2-butyl -1-alkynylcycloalkan-1-ols and derivatives thereof |
US4719043A (en) * | 1986-03-21 | 1988-01-12 | Henkel Kommanditgesellschaft Auf Aktien | Isomeric 1-alkyl/alkenyl-2,2,4(2,4,4)-trimethyl cyclopentan-1-ols as perfumes |
CN101918345A (zh) * | 2008-01-22 | 2010-12-15 | 弗门尼舍有限公司 | 赋予树液和/或泥土类型香调的加香成分 |
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US9290718B2 (en) | 2016-03-22 |
MX2014015175A (es) | 2015-07-02 |
CN104710283A (zh) | 2015-06-17 |
US20160160152A1 (en) | 2016-06-09 |
US20150159118A1 (en) | 2015-06-11 |
BR102014030310B1 (pt) | 2021-12-21 |
BR102014030310A2 (pt) | 2016-08-02 |
EP2902468A2 (en) | 2015-08-05 |
US9701925B2 (en) | 2017-07-11 |
EP2902468B1 (en) | 2017-03-15 |
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