CN105765045A - 香料组合物 - Google Patents
香料组合物 Download PDFInfo
- Publication number
- CN105765045A CN105765045A CN201480064665.7A CN201480064665A CN105765045A CN 105765045 A CN105765045 A CN 105765045A CN 201480064665 A CN201480064665 A CN 201480064665A CN 105765045 A CN105765045 A CN 105765045A
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- CN
- China
- Prior art keywords
- alcohol
- compound
- fragrance
- flavor compositions
- acid
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 149
- 239000002304 perfume Substances 0.000 title abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 40
- 150000001298 alcohols Chemical class 0.000 claims abstract description 11
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 11
- 150000002596 lactones Chemical class 0.000 claims abstract description 8
- 150000002170 ethers Chemical class 0.000 claims abstract description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 6
- 239000000796 flavoring agent Substances 0.000 claims description 73
- 235000019634 flavors Nutrition 0.000 claims description 73
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 22
- 239000004902 Softening Agent Substances 0.000 claims description 20
- 239000002537 cosmetic Substances 0.000 claims description 12
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 85
- 239000003205 fragrance Substances 0.000 abstract description 72
- 241000207199 Citrus Species 0.000 abstract description 8
- 235000020971 citrus fruits Nutrition 0.000 abstract description 8
- BLXFNKYQWNXNTE-UHFFFAOYSA-N 4,7-dimethyloctan-3-ol Chemical compound CCC(O)C(C)CCC(C)C BLXFNKYQWNXNTE-UHFFFAOYSA-N 0.000 abstract 2
- 235000013599 spices Nutrition 0.000 description 42
- -1 2,4-dimethyl-8-nonyl Chemical group 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 29
- 235000019441 ethanol Nutrition 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 21
- 239000002585 base Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 238000011156 evaluation Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 239000000376 reactant Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 241000628997 Flos Species 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 235000010254 Jasminum officinale Nutrition 0.000 description 5
- 240000005385 Jasminum sambac Species 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- PZUDDXJZNSJESK-UHFFFAOYSA-N ethyl 2-cyclohexylpropanoate Chemical compound CCOC(=O)C(C)C1CCCCC1 PZUDDXJZNSJESK-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 230000001953 sensory effect Effects 0.000 description 5
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- SWUIQEBPZIHZQS-UHFFFAOYSA-N calone Chemical compound O1CC(=O)COC2=CC(C)=CC=C21 SWUIQEBPZIHZQS-UHFFFAOYSA-N 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 3
- NVIPUOMWGQAOIT-UHFFFAOYSA-N (E)-7-Hexadecen-16-olide Natural products O=C1CCCCCC=CCCCCCCCCO1 NVIPUOMWGQAOIT-UHFFFAOYSA-N 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-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
- BLOXMGXSDAAJGX-PLNGDYQASA-N (Z)-hex-3-en-1-yl methyl carbonate Chemical compound CC\C=C/CCOC(=O)OC BLOXMGXSDAAJGX-PLNGDYQASA-N 0.000 description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 3
- NVIPUOMWGQAOIT-DUXPYHPUSA-N 7-hexadecen-1,16-olide Chemical compound O=C1CCCCC\C=C\CCCCCCCCO1 NVIPUOMWGQAOIT-DUXPYHPUSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- IPTLKMXBROVJJF-UHFFFAOYSA-N azanium;methyl sulfate Chemical compound N.COS(O)(=O)=O IPTLKMXBROVJJF-UHFFFAOYSA-N 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- 239000004034 viscosity adjusting agent Substances 0.000 description 3
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- WSTQLNQRVZNEDV-CSKARUKUSA-N (e)-4-methyldec-3-en-5-ol Chemical compound CCCCCC(O)C(\C)=C\CC WSTQLNQRVZNEDV-CSKARUKUSA-N 0.000 description 2
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- AWNOGHRWORTNEI-UHFFFAOYSA-N 2-(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethyl acetate Chemical compound CC(=O)OCCC1=CCC2C(C)(C)C1C2 AWNOGHRWORTNEI-UHFFFAOYSA-N 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- HJPCGXGRGNDORH-UHFFFAOYSA-N ethyl sulfate;1h-imidazol-3-ium Chemical compound C1=C[NH+]=CN1.CCOS([O-])(=O)=O HJPCGXGRGNDORH-UHFFFAOYSA-N 0.000 description 1
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- 244000177546 frostweed Species 0.000 description 1
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- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
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- FQMZVFJYMPNUCT-UHFFFAOYSA-N geraniol formate Natural products CC(C)=CCCC(C)=CCOC=O FQMZVFJYMPNUCT-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- SVURIXNDRWRAFU-UHFFFAOYSA-N juniperanol Natural products C1C23C(C)CCC3C(C)(C)C1C(O)(C)CC2 SVURIXNDRWRAFU-UHFFFAOYSA-N 0.000 description 1
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- 229940087305 limonene Drugs 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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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 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
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
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- 230000035772 mutation Effects 0.000 description 1
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- FALTVGCCGMDSNZ-UHFFFAOYSA-N n-(1-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)C1=CC=CC=C1 FALTVGCCGMDSNZ-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
- IZXDTJXEUISVAJ-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH+](C)CCCCCCCCCCCCCCCCCC IZXDTJXEUISVAJ-UHFFFAOYSA-N 0.000 description 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- HIGQPQRQIQDZMP-FLIBITNWSA-N neryl acetate Chemical compound CC(C)=CCC\C(C)=C/COC(C)=O HIGQPQRQIQDZMP-FLIBITNWSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- GJAKJQSIZPJXRS-UHFFFAOYSA-N nonadec-4-en-3-amine Chemical compound CCC(C=CCCCCCCCCCCCCCC)N GJAKJQSIZPJXRS-UHFFFAOYSA-N 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DIRLDPKYOATBIA-UHFFFAOYSA-N oxolan-3-yl acetate Chemical compound CC(=O)OC1CCOC1 DIRLDPKYOATBIA-UHFFFAOYSA-N 0.000 description 1
- OJEQSSJFSNLMLB-UHFFFAOYSA-N p-Tolyl phenylacetate Chemical compound C1=CC(C)=CC=C1OC(=O)CC1=CC=CC=C1 OJEQSSJFSNLMLB-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- FGPPDYNPZTUNIU-UHFFFAOYSA-N pentyl pentanoate Chemical compound CCCCCOC(=O)CCCC FGPPDYNPZTUNIU-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000049 pigment Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000001835 salubrious effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VILMUCRZVVVJCA-UHFFFAOYSA-M sodium glycolate Chemical compound [Na+].OCC([O-])=O VILMUCRZVVVJCA-UHFFFAOYSA-M 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- RBNWAMSGVWEHFP-UHFFFAOYSA-N trans-p-Menthane-1,8-diol Chemical compound CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000015041 whisky Nutrition 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N β-pinene Chemical compound C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 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
- 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
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- 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
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/005—Compositions containing perfumes; Compositions containing deodorants
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
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)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Textile Engineering (AREA)
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Abstract
本发明提供一种含有以下化合物的香料组合物,所述化合物平衡性良好地具有花般的香气和柑橘·绿香的香气,与其它各种香料的调和性优异,通过进行调和能够提高香味、赋予水嫩的花香感。所述香料组合物含有4,7?二甲基辛烷?3?醇。所述香料组合物可以进一步含有例如选自酯类、碳酸酯类、醛类、醚类、内酯类以及4,7?二甲基辛烷?3?醇以外的醇类中的1种以上。
Description
技术领域
本发明涉及一种含有4,7-二甲基辛烷-3-醇的香料组合物。
背景技术
香味是对产品等产生嗜好性或者高级感、安心感、对其效果的期待感等的重要的因素。进一步,有特征的香味赋予识别产品的效果和吸引顾客的作用。特别是花香调在盥洗产品中优选。
芳樟醇、香茅醇、香叶醇等的醇类作为赋予花香调的香料原材料而为人所知。
另一方面,对产品的赋香通常是为了控制香味的平衡性或持续性等而使用混合有多种香料原材料的香料组合物来进行的。构成香料组合物的香料原材料寻求与其它的香料原材料的调和性良好。
作为醇类的例子,作为市售品,3,7-二甲基辛烷-3-醇作为具有花香的香料即四氢芳樟醇出售。
另外,在专利文献1中公开了2,5,7-三甲基-3-辛醇和2,4-二甲基-8-壬醇作为香料有用,并且具有果实般的香调。
在专利文献2中公开了例如3-丁基-6-甲基庚烷-2-醇作为香料有用,并且具有绿水仙和芳香龙胆般的香调。
在专利文献3中公开了3-羟基-4-乙基-7-甲基辛烷具有类似醋栗的新鲜的花般水果般的香调,并且具有草药般的副香。
香料原材料极其大致地如果结构类似则具有类似的香调,但是例如在许多特别是组合多个取代基使之变化的情况下,难以预测其香调会怎样地变化,另外,也难以预测与其它香料原材料的调和性。
现有技术文献
专利文献
专利文献1:日本特开昭54-27506号公报
专利文献2:国际专利第2011/135487号小册子
专利文献3:美国专利3452105号说明书
发明内容
发明所要解决的课题
由于根据香料原材料有与其它的香料成分干涉从而香调变化或变弱的情况,因此,为了提高调香的自由度,希望扩大香料原材料的变种。特别是,花般的香甜华美的香调作为盥洗产品的香味是非常重要的,另外,柑橘类的清爽的香调或具有绿叶的重点的香调也较为重要。期望这些具有花香调,也一并具有柑橘类或绿叶的香调的香料原材料。另一方面,也期望具有有干净感的水嫩的花香的香调,并且适合用于盥洗产品的赋香的香料组合物。
本发明的课题在于提供一种平衡性良好地具有花般的香气和柑橘·绿香的香气,与其它各种香料的调和性优异,通过进行调和能够提高香味、赋予水嫩的花香感的香料组合物。
解决课题的技术手段
本发明者们发现:特定结构的脂肪族饱和醇平衡性良好地具有花般的香气和柑橘·绿香的香气,与其它各种香料的调和性优异,通过进行调和能够提高香味、赋予水嫩的花香感,从而完成本发明。
即,本发明为含有4,7-二甲基辛烷-3-醇的香料组合物。
发明的效果
本发明的香料组合物由于含有4,7-二甲基辛烷-3-醇,因此,与其它各种香料的调和性优异,通过进行调和能够提高香味、赋予水嫩的花香感。
具体实施方式
[4,7-二甲基辛烷-3-醇的制造方法]
本发明的4,7-二甲基辛烷-3-醇(以下述式(I)表示。在本说明书中,有时称为化合物(I))可以利用一般的有机化学反应进行合成,对其制造方法不进行限制。例如,化合物(I)可以利用包括使用异戊醛(以下述式(III)表示。在本说明书中,有时称为化合物(III))和3-戊酮(以下述式(IV)表示。在本说明书中,有时称为化合物(IV))进行交叉羟醛加成反应,接着进行脱水、还原,得到化合物(I)的工序的方法进行制造(参照方案1)。
在所述制造方法中,首先,使用异戊醛(III)和3-戊酮(IV)在碱催化剂存在下进行交叉羟醛加成反应。作为碱催化剂,优选为碱金属的氢氧化物,进一步优选为氢氧化钠。反应例如在15~30℃的温度下进行例如1小时~60小时的时间。
特别是从收率良好地进行交叉羟醛加成反应的观点出发,优选在反应溶液中进一步添加水。
接着,将得到的生成物脱水。脱水优选在反应液中添加磷酸等,在水的沸点以上进行。在使反应体系的压力进行变化的情况下,优选该压力为水的沸点以上进行。1个大气压(101kPa)下优选例如在110~160℃下加热来进行。
通过脱水,可以得到4,7-甲基辛-4-烯-3-酮(以所述式(II)表示。在本说明书中,有时称为化合物(II))。
接着,将化合物(II)还原,得到化合物(I)。还原方法只要是通常的还原方法就不特别地限制,但从提高纯度的观点出发,优选为使用了贵金属催化剂的加氢方法。具体来说,还原可以在钌、钯、铂等贵金属催化剂存在下在氢气氛下进行加氢。加氢例如优选在0.1~5MPa的氢压力下在50~170℃的温度下进行,进一步优选在60~160℃的温度下进行,更加优选在80~160℃的温度下进行。另外,作为加氢的反应时间,例如进行3~80小时。
由此,可以以高纯度得到化合物(I)。得到的化合物(I)的香调平衡性良好地具有花般(特别是铃兰花的香气)和柑橘·绿香的香气。
[香料组合物]
本发明的香料组合物含有如上所述的4,7-二甲基辛烷-3-醇(化合物(I))。化合物(I)的含量在香料组合物中优选为0.01~100质量%,进一步优选为0.1~15质量%,更加优选为0.3~5质量%。通过含有0.01~100质量%的化合物(I),可以对香料组合物赋予更强烈的花香感。
另外,本发明的香料组合物可以含有通常使用的其它的香料成分或所希望的组成的调和香料作为化合物(I)以外的香料。通过含有化合物(I)以外的香料,可以对本发明的香料组合物赋予例如花香调、百花香调、风信子香调、天竺葵香调、玫瑰香调、佛手柑香调、兰花香调、铃兰香调(铃兰花)的香气。
在本发明的香料组合物中,作为能够与化合物(I)组合使用的其它的香料,可以列举化合物(I)以外的醇类、烃类、酚类、酯类、碳酸酯类、醛类、酮类、缩醛类、醚类、羧酸、内酯类、腈类、席夫碱类、天然精油或天然提取物等的香料成分。
这些中,优选为化合物(I)以外的醇类、酯类、碳酸酯类、醛类、酮类、醚类和内酯类,其中,更优选为化合物(I)以外的醇类、酯类。
作为化合物(I)以外的醇类,可以列举萜类醇、芳香族醇、脂肪族醇等。这些中,优选为萜类醇、芳香族醇。
作为萜类醇,可以列举芳樟醇、香茅醇、香叶醇、橙花醇、萜品醇、α-萜品醇、二氢月桂烯醇、金合欢醇、橙花叔醇、雪松醇、薄荷醇、冰片等。
作为芳香族醇,可以列举苯乙基醇、苄醇、二甲基苄基甲醇、苯基乙基二甲基甲醇、苯基己醇等。
作为脂肪族醇,可以列举顺式-3-己烯醇、1-(2,2,6-三甲基环己基)-3-己醇、琥珀芯(AMBERCORE)(花王株式会社商品名,1-(2-叔丁基环己氧基)-2-丁醇)、白雷曼檀香(SANDALMYSORECORE)(花王株式会社商品名,2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇)、木兰醇(MAGNOL)(花王株式会社的商品名,以3(4)-(5-乙基双环[2,2,1]庚基-2)-环己醇为主成分的混合物)、UNDECAVERTOL(GivaudanRoureK.K.的商品名,4-甲基-3-癸烯-5-醇)、莰基环已醇。
作为烃类,可以列举柠檬烯、α-蒎烯、β-蒎烯、萜品烯、柏木烯、长叶烯、瓦伦烯等。
作为酚类,可以列举愈创木酚、丁子香酚、异丁子香酚、百里酚、对甲酚、香兰素、乙基香兰素等。
作为酯类,可以列举甲酸酯、乙酸酯、丙酸酯、丁酸酯、戊酸酯、己酸酯、庚酸酯、壬酸酯、苯甲酸酯、肉桂酸酯、水杨酸酯、巴西基酸酯、惕各酸酯、茉莉酸酯、缩水甘油酸酯、邻氨基苯甲酸酯等。
这些酯类中,优选使用乙酸酯、丙酸酯、水杨酸酯、茉莉酸酯。
作为甲酸酯,可以列举甲酸芳樟酯、甲酸香茅酯、甲酸香叶酯等。
作为乙酸酯,可以列举乙酸己酯、乙酸顺式-3-己烯酯、乙酸芳樟酯、乙酸香茅酯、乙酸香叶酯、橙花醇乙酸酯、乙酸萜品酯、乙酸诺卜酯(nopylacetate)、乙酸冰片酯、乙酸异冰片酯、乙酰基丁子香酚、乙酰基异丁子香酚、邻叔丁基环己基乙酸酯、对叔丁基环己基乙酸酯、乙酸三环癸烯酯、乙酸苄酯、乙酸苯乙酯、乙酸苏合香酯、乙酸肉桂酯、乙酸二甲基苄基原酯、乙酸苯乙基苯基酯、3-戊基四氢呋喃-4-基乙酸酯、苯乙酸对甲酚酯等。
作为丙酸酯,可以列举丙酸香茅酯、丙酸三环癸烯酯、丙酸烯丙基环己基酯、丙酸乙基2-环己基酯、丙酸苄酯、丙酸苏合香酯等。
作为丁酸酯,可以列举丁酸香茅酯、正丁酸二甲基苄基原酯、异丁酸三环癸烯酯等。
作为戊酸酯,可以列举戊酸甲酯、戊酸乙酯、戊酸丁酯、戊酸戊酯、戊酸苄酯、戊酸苯乙酯等;作为己酸酯,可以列举己酸甲酯、己酸乙酯、己酸烯丙酯、己酸芳樟酯、己酸香茅酯等。
作为庚酸酯,可以列举庚酸甲酯、庚酸烯丙酯等。
作为壬酸酯,可以列举2-壬酸甲酯、2-壬酸乙酯、3-壬酸乙酯等。
作为苯甲酸酯,可以列举苯甲酸甲酯、苯甲酸苄酯、3,6-二甲基苯甲酸酯等。
作为肉桂酸酯,可以列举肉桂酸甲酯、肉桂酸苄酯等。
作为水杨酸酯,可以列举水杨酸甲酯、水杨酸正己基酯、水杨酸顺式-3-己烯基酯、水杨酸环己酯、水杨酸苄酯等。
进一步,作为巴西酸酯,可以列举巴西酸乙二醇酯等。
作为惕各酸酯,可以列举惕各酸香叶酯、1-己基惕各酸酯、顺式-3-己烯基惕各酸酯等。
作为茉莉酸酯,可以列举茉莉酸甲酯、二氢茉莉酸甲酯等。
作为缩水甘油酸酯,可以列举甲基2,4-二羟基-乙基甲基苯基缩水甘油酸酯、4-甲基苯基乙基缩水甘油酸酯等。
作为邻氨基苯甲酸酯,可以列举邻氨基苯甲酸甲酯、邻氨基苯甲酸乙酯、邻氨基苯甲酸二甲酯等。
进一步,作为其它的酯,可以列举橡苔1号(Methylatrarate)、烯丙基环己基乙醇酸酯、果香酯(FRUITATE)(花王株式会社商品名,三环[5.2.1.0]癸烷-2-羧酸乙酯)、POIRENATE(花王株式会社商品名,2-环己基丙酸乙酯)、PERANAT(花王株式会社商品名,2-甲基戊酸-2-甲基戊酯)、MELUSAT(花王株式会社商品名,3,5,5-三甲基己酸乙酯)、IROTYL(花王株式会社商品名,2-乙基己酸乙酯,超链接“http://techterm.astamuse.com/ja/己酸?from=patent#techterm”)等。
作为碳酸酯类,可以列举绿花芬(LIFFAROME)(IFF公司商品名,顺式-3-己烯基甲基碳酸酯)、JASMACYCLAT(花王株式会社商品名,甲基-环辛基碳酸酯)、FLORAMAT(花王株式会社商品名,乙基-2-叔丁基环己基碳酸酯)等。
作为醛类,可以列举正辛醛、正壬醛、正癸醛、正十二醛、2-甲基十一醛、10-十一烯醛、香茅醛、柠檬醛、羟基香茅醛、女贞醛(Triplal)(IFF公司商品名,2,4-二甲基-3-环己烯基甲醛)、Cyclovertal(花王株式会社商品名,二甲基-3-环己烯基-1-甲醛)、苯甲醛、苯基乙醛、苯基丙醛、肉桂醛、二甲基四氢苯甲醛、波洁红醛(BOURGEONAL)(Givaudan公司商品名,3-(对叔丁基苯基)-丙醛)、Lyral(IFF的商品名,羟基柑青醛)、POLLENALII(花王株式会社商品名,2-环己基丙醛)、铃兰醛(Lilial)(Givaudan公司商品名,对叔丁基-α-甲基氢化肉桂醛)、对异丙基-α-甲基氢化肉桂醛、海风醛(Floralozone)(IFF公司商品名,对乙基-α,α-二甲基氢化肉桂醛)、α-戊基肉桂醛、α-己基肉桂醛、己基肉桂醛、洋茉莉醛(Heliotropin)、新洋茉莉醛(Helional)(IFF公司商品名,α-甲基-3,4-亚甲基二氧基氢化肉桂醛)等。
作为酮类,可以列举α-紫罗兰酮、β-紫罗兰酮、γ-紫罗兰酮、α-甲基紫罗兰酮、β-甲基紫罗兰酮、γ-甲基紫罗兰酮、大马酮、甲基庚烯酮、4-亚甲基-3,5,6,6-四甲基-2-庚酮、苯乙酮、戊基环戊酮、二氢茉莉酮、玫瑰酮、香芹酮、薄荷酮、樟脑、乙酰基柏木烯、异长叶烷酮、诺卡酮、苄基丙酮、茴香基丙酮、甲基β-萘酮、2,5-二甲基-4-羟基-3(2H)-呋喃酮、麦芽酚、麝香酮、灵猫酮、环十五酮、西瓜酮(Calone)(FirmenichInc.商品名,7-甲基-3,4-二氢-2H-苯并二氧环丙-3-酮)、覆盆子酮、甲基-b-萘酮、洋茉莉基丙酮(Heliotropylacetone)等。
作为缩醛类,可以列举乙醛乙基苯基丙基缩醛、柠檬醛二乙缩醛、苯基乙醛甘油基缩醛、乙酰乙酸乙酯乙二醇缩醛、BOISAMBRENEFORTE(花王株式会社商品名)、TROENAN(花王株式会社商品名)等。
作为醚类,可以列举乙基芳樟醇、柏木基甲基醚、草蒿脑、茴香脑、β-萘甲醚、β-萘乙醚、氧化柠檬烯、玫瑰醚(Roseoxide)、氧化橙花醇、1,8-桉叶素、玫瑰呋喃、降龙涎香醚(AMBROXAN)(花王株式会社商品名,十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃)、HERBAVERT(花王株式会社商品名,3,3,5-三甲基环己基乙基醚)、佳乐麝香(Galaxolide)(IFF公司商品名,六甲基六氢环戊二烯苯并吡喃)、苯乙醛二甲缩醛等。
作为羧酸类,可以列举苯甲酸、苯基乙酸、肉桂酸、氢化肉桂酸、丁酸、2-己烯酸等。
作为内酯类,可以列举γ-癸内酯、δ-癸内酯、γ-戊内酯、γ-壬内酯、γ-十一内酯、δ-己内酯、γ-茉莉内酯、威士忌内酯(whiskylactone)、香豆素、环十五内酯、环十六内酯、黄葵内酯(Ambrettolide)、11-氧杂十六内酯、丁烯基酞内酯等。
作为腈类,可以列举香叶腈、香茅腈、十二腈等。
作为席夫碱类,可以列举AURANTIOL、LIGANTRAL等。
作为天然精油或天然提取物,可以列举橘子、柠檬、酸橙、佛手柑、香草、橘皮、薄荷、留兰香、薰衣草、甘菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、岩蔷薇、天竺葵、茉莉、依兰、茴芹、丁香、生姜、肉豆蔻、小豆蔻、雪松、扁柏、香根草、广藿香、柠檬草、劳丹脂、葡萄柚等。
这些的化合物(I)以外的其它的香料的含量可以根据调和香料的种类、作为目的的香气的种类和香气的强度等来适当选择,在香料组合物中分别优选为0.0001~99.99质量%,进一步优选为0.001~80质量%。另外,其它的香料的合计含量在香料组合物中优选为5~99.99质量%,进一步优选为50~99.95质量%。
本发明的香料组合物作为含有4,7-二甲基辛烷-3-醇(化合物(I))以及其它香料原材料的基体,可以含有其自身不具有气味的油剂。所述油剂使香料成分均匀地混合,容易配合于产品中,容易将适度强度的香味赋香。作为所述油剂的具体例子,可以列举乙二醇、丙二醇、丁二醇、二丙二醇等的多元醇类、肉豆蔻酸异丙酯、己二酸二丁酯、癸二酸二乙酯等的酯类、液体石蜡、角鲨烷等的烃类。所述油剂的含量在香料组合物中优选为1~95质量%,进一步优选为10~80质量%,更加优选为15~50质量%。
另外,本发明的香料组合物也可以含有聚氧乙烯烷基醚、山梨糖醇酐脂肪酸酯等的表面活性剂。
[作为赋香成分的用途]
含有本发明的4,7-二甲基辛烷-3-醇(化合物(I))的香料组合物可以作为强烈地具有水嫩花香感的调合香料,作为各种产品的赋香成分使用。因此,本发明是作为香料使用含有4,7-二甲基辛烷-3-醇(化合物(I))的香料组合物的方法。作为该化合物的使用方法,单独或者与其它成分组合而含有于皂、化妆品、毛发化妆品、洗涤剂、柔软剂、喷雾产品、芳香剂、香水、沐浴剂等的盥洗产品的基体中。因此,本发明是作为皂、化妆品、毛发化妆品、洗涤剂、柔软剂、喷雾产品、芳香剂、香水、沐浴剂等的盥洗产品的香料,使用含有4,7-二甲基辛烷-3-醇(化合物(I))的香料组合物的方法。
在所述使用方法中,在香料组合物含有4,7-二甲基辛烷-3-醇(化合物(I))的情况下,以化合物(I)相对于香料组合物整体优选为0.01~100质量%,进一步优选为0.1~15质量%,更加优选为0.3~5质量%的量使用。通过含有0.01~100质量%的化合物(I),可以赋予更强烈的花香感。
其中,优选将含有本发明的4,7-二甲基辛烷-3-醇(化合物(I))的香料组合物对毛发或衣物等纤维进行处理来赋予花般的香味,作为能够作为赋香成分优选使用的产品,可以列举洗发剂、护发剂等的毛发化妆品、衣物用的柔软剂。
因此,本发明还提供一种含有本发明的香料组合物的清洁剂组合物、含有本发明的香料组合物的化妆品、含有本发明的香料组合物的纤维处理组合物、含有本发明的香料组合物的芳香除臭剂、以及含有本发明的香料组合物的清扫用无纺布。
作为本发明的清洁剂组合物,优选为身体用清洁剂组合物、衣料用清洁剂组合物、硬质表面用清洁剂组合物,进一步优选为身体用清洁剂组合物、衣料用清洁剂组合物,更加优选为衣料用清洁剂组合物。另外,作为本发明的清洁剂组合物,可以列举粉末清洁剂组合物、液体清洁剂组合物,优选为液体清洁剂组合物。
作为身体用清洁剂组合物的例子,可以列举皮肤用清洁剂组合物、毛发用清洁剂组合物,优选为皮肤用清洁剂组合物。
作为硬质表面用清洁剂组合物的例子,可以列举多用途清洁剂(AllPurposeCleaner)、餐具用清洁剂组合物。
作为本发明的纤维处理组合物,优选为柔软剂。
作为本发明的化妆品,优选为香水、身体用化妆品、毛发用化妆品。
本发明的柔软剂包含例如季铵盐和本发明的香料组合物。所述柔软剂可以进一步包含杀菌剂、粘度调节剂、pH调节剂、溶剂等。
作为所述季铵盐,只要是现有公知的季铵盐就可以使用。例如,可以列举辛基三甲基氯化铵、十二烷基三甲基氯化铵、十六烷基三甲基氯化铵、牛油三甲基氯化铵、椰油三甲基氯化铵、辛基二甲基苄基氯化铵、十二烷基二甲基苄基氯化铵、双十八烷基二甲基氯化铵、二硬脂酰氧基乙基二甲基氯化铵、二油酰氧基乙基二甲基氯化铵、N-硬脂酰氧基乙基-N,N-二甲基-N-(2–羟基乙基)甲基硫酸铵、N,N-二硬脂酰氧基乙基-N-甲基-N-(2-羟基乙基)甲基硫酸铵、N-油酰氧基乙基-N,N-二甲基-N-(2-羟基乙基)甲基硫酸铵、二硬脂基甲基胺盐酸盐、二油基甲基胺盐酸盐、二硬脂基甲基胺盐酸盐、N-(3-十八酰基氨基丙基)-N-(2-十八酰氧基乙基)-N-甲基胺盐酸盐、甲基-1-牛油酰胺乙基-2-牛油烷基咪唑鎓甲基硫酸盐、甲基-1-十六酰基酰胺乙基-2-十五烷基氯化咪唑、乙基-1-十八碳烯酰基酰胺乙基-2-十七碳烯基咪唑鎓乙基硫酸盐、1-十八酰基氨基乙基-2-十七烷基咪唑啉盐酸盐、1-十八酰基氨基乙基-2-十七碳烯基咪唑啉盐酸盐、N,N-二[2-(烷酰氧基)-乙基]-N-(2-羟基乙基)-N-甲基硫酸铵等。这些可以单独使用1种或者将2种以上组合使用。
作为所述杀菌剂,例如可以列举碳原子数为1~8的醇、苯甲酸类、酚类等,具体来说,可以列举乙醇、丙二醇、苄醇、水杨酸、对羟基苯甲酸甲酯、甲酚等。
作为所述粘度调节剂,可以使用无机或有机的盐类(不包括季铵盐)。具体来说,可以列举氯化钠、氯化钾、氯化钙、氯化镁、氯化铝、硫酸钠、硫酸镁、硫酸钾、硝酸钠、硝酸镁、对甲苯磺酸钠、乙醇酸钠、乙酸钠、乙酸钾、乙醇酸钾、乳酸钠等。优选为氯化钙、氯化镁。
本发明的柔软剂含有水,通常组合物的剩余部分为水。作为水,优选为离子交换水和蒸馏水。本发明的柔软剂在20℃下的pH优选为1.5~6。从防腐·杀菌力的观点出发,pH越低越好,但如果过低,则通常配合于组合物中的成分有可能会发生分解。因此,进一步优选pH为1.5~5,更加优选为2~4.5。
本发明的柔软剂的pH调节中可以使用任意的无机或有机的酸和碱。
进一步,在本发明的柔软剂中,作为上述成分以外的其它的任意成分,可以在不妨碍发明的效果的范围内配合通常配合于柔软剂中的公知的成分。作为任意成分,例如可以配合硬脂酸、油酸、棕榈酸等的高级脂肪酸或这些与低级醇的酯等,可以配合硬脂酸与甘油等的酯即脂肪酸甘油酯等的非离子表面活性剂,可以配合硬脂醇、棕榈醇、油醇等的高级醇,可以配合乙二醇或甘油等的低温稳定化剂,其它可以配合尿素、颜料、纤维素衍生物、紫外线吸收剂、荧光增白剂等。
在本发明的清洁剂组合物中,除了含有含有4,7-二甲基辛烷-3-醇的香料组合物以外,优选含有阴离子表面活性剂,进一步可以配合非离子表面活性剂、pH调节剂、粘度调节剂、溶剂、油剂、防腐剂、水等。
在本发明的香水中,除了含有4,7-二甲基辛烷-3-醇的香料组合物以外,可以配合溶剂、水等。
本发明提供一种4,7-二甲基辛烷-3-醇(化合物(I))。4,7-二甲基辛烷-3-醇(化合物(I))如上所述平衡性良好地具有花般(特别是铃兰花的香气)和柑橘·绿香的香气。因此,本发明是将4,7-二甲基辛烷-3-醇(化合物(I))作为赋香成分使用的方法。另外,提供一种将4,7-二甲基辛烷-3-醇(化合物(I))作为赋香成分使用的方法。
关于上述的实施方式,本发明进一步公开以下的香料组合物、制造方法、使用的方法以及用途。
<1>一种香料组合物,其中,含有4,7-二甲基辛烷-3-醇。
<2>如上述<1>所述的香料组合物,其中,4,7-二甲基辛烷-3-醇的含量优选为0.01~100质量%,进一步优选为0.1~15质量%,更加优选为0.3~5质量%。
<3>如上述<1>或<2>所述的香料组合物,其中,进一步含有4,7-二甲基辛烷-3-醇以外的醇类、酯类、碳酸酯类、醛类、酮类、醚类以及内酯类中的1种以上。
<4>如上述<3>所述的香料组合物,其中,所述酯类为选自乙酸酯、丙酸酯、水杨酸酯、茉莉酸酯、橡苔1号、果香酯(FRUITATE)以及POIRENATE中的1种以上。
<5>如上述<1>~<4>中任一项所述的香料组合物,其中,所述碳酸酯为绿花芬(LIFFAROME)。
<6>如上述<3>~<5>中任一项所述的香料组合物,其中,所述醛类为选自女贞醛、波洁红醛、铃兰醛、海风醛、己基肉桂醛以及新洋茉莉醛中的1种以上。
<7>如上述<3>~<6>中任一项所述的香料组合物,其中,所述酮类为选自β-紫罗兰酮、大马酮、麝香酮、西瓜酮、覆盆子酮、甲基-β-萘酮和洋茉莉基丙酮中的1种以上。
<8>如上述<3>~<7>中任一项所述的香料组合物,其中,所述醚类为选自乙基芳樟醇、玫瑰醚、降龙涎香醚、佳乐麝香以及苯乙醛二甲缩醛中的1种以上。
<9>如上述<3>~<8>中任一项所述的香料组合物,其中,所述内酯类为黄葵内酯。
<10>如上述<3>~<9>中任一项所述的香料组合物,其中,4,7-二甲基辛烷-3-醇以外的醇类香料为选自萜类醇和脂肪族醇中的1种以上。
<11>如上述<1>~<10>中任一项所述的香料组合物,其中,进一步含有油剂。
<12>如上述<1>~<11>中任一项所述的香料组合物,其中,进一步含有表面活性剂。
<13>一种纤维处理组合物(优选为柔软剂),其中,含有上述<1>~<12>中任一项所述的香料组合物。
<14>如上述<13>所述的纤维处理组合物(优选为柔软剂),其中,进一步含有季铵盐、杀菌剂、粘度调节剂、pH调节剂和/或溶剂。
<15>一种化妆品(优选为香水、身体用化妆品、毛发化妆品),其中,含有上述<1>~<12>中任一项所述的香料组合物。
<16>一种清洁剂组合物(优选为身体用清洁剂组合物(例如,皮肤用清洁剂组合物、毛发用清洁剂组合物)、衣料用清洁剂组合物、硬质表面用清洁剂组合物(例如,多用途清洁剂(AllPurposeCleaner)、餐具用清洁剂组合物),进一步优选为身体用清洁剂组合物、衣料用清洁剂组合物,更加优选为衣料用清洁剂组合物),其中,含有上述<1>~<12>中任一项所述的香料组合物。
<17>一种清洁剂组合物(优选为粉末清洁剂组合物、液体清洁剂组合物,进一步优选为液体清洁剂组合物),其中,含有上述<1>~<12>中任一项所述的香料组合物。
<18>一种芳香除臭剂,其中,含有上述<1>~<12>中任一项所述的香料组合物。
<19>一种清扫用无纺布,其中,含有上述<1>~<12>中任一项所述的香料组合物。
<20>一种4,7-二甲基辛烷-3-醇的制造方法,其中,包括使用异戊醛和3-戊酮进行交叉羟醛加成反应,接着进行脱水、还原,得到4,7-二甲基辛烷-3-醇的工序。
<21>4,7-二甲基辛烷-3-醇。
<22>上述<1>~<12>中任一项所述的香料组合物作为赋香成分的用途。
<23>一种将4,7-二甲基辛烷-3-醇作为赋香成分使用的方法。
实施例
在以下的制造例等中,以下一并表示进行过的测定法的详细情况。
[化合物的鉴定]
通过核磁共振光谱(1H-NMR)鉴定以下的制造例等中得到的各化合物的结构。核磁共振光谱使用氯仿-d作为溶剂,通过Varian公司制造的产品名称“Mercury400”进行测定。
[制造例1]
4,7-甲基辛-4-烯-3-酮(化合物(II))的制造
在烧瓶中加入氢氧化钠(0.1g)、水(20g)和3-戊酮(IV)(50g、0.58mol),维持在15℃,一边进行搅拌一边用5小时滴加异戊醛(III)(20g、0.23mol),追加添加氢氧化钠(0.2g),进一步在25℃下搅拌48小时。搅拌之后,将反应液静置除去下层之后,从上层馏去过量的3-戊酮(IV)。
接着,在反应液上层部分加入85%磷酸(1g),在烧瓶中安装水分馏装置加热至120℃进行脱水。在脱水后的反应液中加入氢氧化钠(0.7g)进行中和,加入硫酸镁进行干燥之后,通过过滤除去硫酸镁。将得到的反应液浓缩,得到残留物(23g)。
使用硅胶柱(展开溶剂:己烷:乙酸乙酯=99:1(v/v))将得到的残留物进行精制。通过进一步蒸馏将得到的精制物进行精制,得到20g化合物(II)。
得到的化合物(II)的纯度为97%。
[制造例2]
4,7-二甲基辛烷-3-醇(化合物(I))的制造
在加氢用耐压烧瓶中加入5%活性碳担载钌催化剂(0.06g)、异丙醇(1.0g)和制造例1中得到的化合物(II)(1.0g),在90℃、0.5MPa的氢压下进行加氢18小时。将得到的反应液过滤,得到滤液2g(收率95%)。
将得到的滤液浓缩,通过蒸馏将得到的浓缩液精制,得到0.8g化合物(I)。得到的化合物(I)的纯度为99%。
以下显示化合物(I)的1H-NMR的测定结果。
1H-NMR(CDCl3,400MHz,δppm):0.80-0.90(m,9H)、0.96(dt、J=7.2Hz、5.2Hz、3H)、1.05-1.60(m,9H)、3.30-3.45(m,1H)
[比较制造例1]
2,5-二甲基己烷-1-醇(在本说明书中,有时称为化合物(VI))的制造
在烧瓶中加入哌啶(0.9g)、庚酸(1.4g)和异戊醛(III)(20g),一边进行搅拌一边在75℃下用3小时滴加丙醛(V)(10g)。将得到的反应液冷却之后,进行分层,除去下层之后,在上层加入乙酸(1g)和水(3g),进行中和。在得到的上层中加入硫酸镁进行干燥之后,通过过滤除去硫酸镁。将得到的反应液浓缩,得到2,5-二甲基己基-2-烯醛(在本说明书中,称为化合物(VIII))(20g)(化合物(VIII)的收率为66%)。
在烧瓶中加入甲醇(20g)、50%氢氧化钠水溶液(0.2g)、水(8g)、硼氢化钠(2g),在15℃下用0.5小时滴加化合物(VIII)(20g),进一步搅拌0.5小时。在反应液中加入6N硫酸水溶液(20mL)分解过量的硼氢化钠,进一步加入50%氢氧化钠水溶液(5g),将反应液调成中性。其后,从反应液中在大气压下馏去甲醇,在残留液中加入硫酸镁进行干燥之后,通过过滤除去硫酸镁。将得到的残留液浓缩,得到浓缩液14g(2,5-二甲基己基-2-烯-1-醇的收率为81%)。用硅胶柱(展开溶剂:己烷:乙酸乙酯=97:3(v/v))将得到的浓缩液精制,得到2,5-二甲基己基-2-烯-1-醇(在本说明书中称为化合物(VII))(1.4g)。得到的化合物(VII)的纯度为98%。
在加氢用耐压烧瓶中加入5%活性碳担载钌催化剂(0.02g)、异丙醇(1.2g)和化合物(VII)(0.3g),在90℃、0.5MPa的氢压下进行加氢3小时。进行得到的反应液的过滤,得到滤液(0.3g)(收率88%)。
将得到的滤液浓缩,通过蒸馏将得到的浓缩液精制,得到0.1g2,5-二甲基己烷-1-醇(VI)。得到的化合物(VI)的纯度为100%。
以下显示化合物(VI)的1H-NMR的测定结果。
1H-NMR(CDCl3,400MHz,δppm):0.88(d、J=6.4Hz、3H)、0.88(d、J=6.4Hz、3H)、0.92(d、J=6.4Hz、3H)、1.02-1.30(m,4H)、1.32-1.64(m,3H)、3.38-3.54(m,2H)
[比较制造例2]
2,5-二甲基-2-乙基己烷-1-醇(在本说明书中,有时称为化合物(XI))的制造
在烧瓶中加入甲苯(20mL)、氢氧化钠(10g)、四丁基碘化铵(TBAI)(1.3g)以及水(10mL),在70℃下用1小时滴加2-甲基丁醛(IX)(21g)和1-氯-3-甲基-2-丁烯(X)(31g),然后,用水和乙醚分层。用亚硫酸钠水溶液水洗上层(有机层),加入硫酸镁进行干燥之后,通过过滤除去硫酸镁。将得到的有机层浓缩,得到2-乙基-2,5-二甲基己基-4-烯醛(在本说明书中有时称为化合物(XIII))(42g)。
在烧瓶中加入甲醇(5g)、50%氢氧化钠水溶液(1g)、水(1g)和硼氢化钠(0.5g),在15℃下用0.5小时滴加化合物(XIII),其后,搅拌1小时。在得到的反应液中加入6N的硫酸水溶液,分解过量的硼氢化钠,进一步加入50%氢氧化钠水溶液将反应液调成中性。其后,在大气压下从反应液中馏去甲醇。在得到的残留液中加入硫酸镁进行干燥之后,通过过滤除去硫酸镁。将得到的残留液浓缩,得到3.8g浓缩液(2-乙基-2,5-二甲基己基-4-烯-1-醇的收率63%)。用硅胶柱(展开溶剂:己烷:乙酸乙酯=97:3(v/v))将得到的浓缩液精制,得到2-乙基-2,5-二甲基己基-4-烯-1-醇(在本说明书中称为化合物(XII))(2g)。化合物(XII)的纯度为100%。
在加氢用耐压烧瓶中加入5%活性碳担载钌催化剂(0.03g)、异丙醇(1.2g)和化合物(XII)(0.5g),在90℃、0.5MPa的氢压下进行加氢2.5小时。将得到的反应液过滤,得到滤液(0.83g)(收率99%)。
将得到的滤液浓缩,通过蒸馏将得到的浓缩液精制,得到0.5g化合物(XI)。得到的化合物(XI)的纯度为100%。
以下显示化合物(XI)的1H-NMR的测定结果。
1H-NMR(CDCl3,400MHz,δppm):0.81(t、J=7.6Hz、3H)、0.81(s、3H)、0.89(d、J=6.8Hz、6H)、1.05-1.35(m,6H)、1.35-1.50(m,1H)、3.34(d、J=6.0Hz、2H)
[香料原材料的香气评价]
按照下述香气评价方法进行制造例2中得到的化合物(I)的香气评价。
化合物(I)的香气评价由有7年调香和香料评价业务经验的熟练者1名通过闻香纸法判定香调。将闻香纸(宽度为6mm、长度为150mm的香料试纸)的前端约5mm浸渍于样品中,进行评价。
对于香气,从更强烈地感觉到的开始依次列举主要感觉到的香味(主香气),进一步备注次要感觉到的香味(副香气)。另外,还对于有无花香感进行判定。
代替制造例2中得到的化合物(I)而使用比较制造例1中得到的化合物(VI)、比较制造例2中得到的化合物(XI)以及下述式(XIV)所表示的3,7-二甲基辛烷-3-醇(四氢芳樟醇)(在本说明书中,有时称为化合物(XIV)),与制造例2中得到的化合物(I)同样地进行香气评价。
[表1]
如所述表1所示,可以确认,本发明的化合物(I)具有花般的主香气,除此以外,平衡性良好地具有柑橘、进一步绿香的香气。
实施例1(柔软剂)
使用制造例2中得到的化合物(I),调制表2所示的组成的柔软剂。对于该柔软剂,进行以下的香气评价。
[香气评价]
由有7年调香和香料评价业务经验的熟练者1名,在容量为100毫升的玻璃制瓶中加入50毫升表2所示的组成的柔软剂,密封,在25℃下放置24小时之后,评价开封时的瓶口的香气。
对于香气,从更强烈地感觉到的开始依次列举主要感觉到的香味(主香气),对于判断还进行备注。
[表2]
如上述表2所示,可以确认含有本发明的香料组合物的柔软剂可以得到水嫩且强烈的花香感。
实施例2和比较例1~4(香水用香料组合物)
使用制造例2中得到的化合物(I),调制表3所示的组成的香水用的香料组合物(实施例2)。另外,作为比较例,使用不包括化合物(I)的香料组合物(比较例1)、进一步比较制造例1中得到的化合物(VI)(比较例2)、比较制造例2中得到的化合物(XI)(比较例3)以及化合物(XIV)(比较例4),制造表3所示的组成的香水用的香料组合物。香料组合物的香气评价用与制造例2中得到的化合物(I)的评价同样的方法进行,通过感官评价进行用于香水中的情况下的判定。将感官评价的结果示于表4中。
[表3]
1)绿花芬(LIFFAROME):IFF公司(商品名),化合物名:顺式-3-己烯基甲基碳酸酯
2)西瓜酮:Firmenich公司(商品名),化合物名:7-甲基-3,4-二氢-2H-苯并二氧环丙-3-酮
3)海风醛:IFF公司(商品名),化合物名:对乙基-α,α-二甲基氢化肉桂醛
4)新洋茉莉醛:IFF公司(商品名),化合物名:α-甲基-3,4-亚甲基二氧基氢化肉桂醛
5)波洁红醛(BOURGEONAL):Givaudan公司(商品名),化合物名:3-(对叔丁基苯基)-丙醛
6)铃兰醛:Givaudan公司(商品名),化合物名:对叔丁基-α-甲基氢化肉桂醛
7)琥珀芯(AMBERCORE):花王株式会社(商品名),化合物名:1-(2-叔丁基环己氧基)-2-丁醇
8)白雷曼檀香(SANDALMYSORECORE):花王株式会社(商品名),化合物名:2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇
[表4]
比较例1 | 新鲜并且具有甜味的水生植物-花般 |
实施例2 | 使人想起铃兰花,并且赋予清洁感和水嫩感 |
比较例2 | 有草药般的青草气味,花香感受损 |
比较例3 | 有木质般的涩味,花香感受损14 --> |
比较例4 | 虽然有花香感和甜味,但是水嫩感不足 |
如上述表4所示,可以确认本发明的香料组合物通过含有进一步的香料成分,可以得到具有清洁感和水嫩感的花香调。
实施例3和比较例5~8(衣料用液体洗涤剂用香料组合物)
使用制造例2中得到的化合物(I),调制表5所示的组成的白色花香型的衣料用液体洗涤剂用的香料组合物。另外,作为比较例,使用不包括化合物(I)的香料组合物(比较例5)、进一步比较制造例1中得到的化合物(VI)(比较例6)、比较制造例2中得到的化合物(XI)(比较例7)以及化合物(XIV)(比较例8),制造表5所示的组成的白色花香型的衣料用液体洗涤剂用的香料组合物。香气评价用与制造例2中得到的化合物(I)的评价同样的方法进行,通过感官评价进行用于洗涤剂中的情况下的判定。将感官评价的结果示于表6中。
[表5]
1)女贞醛:IFF公司(商品名),化合物名:2,4-二甲基-3-环己烯-1-甲醛
2)木兰醇(MAGNOL):花王株式会社(商品名),以乙基降冰片基环己醇为主成分的混合物
3)UNDECAVERTOL:GivaudanRoureK.K.(商品名),化合物名:4-甲基-3-癸烯-5-醇
4)POIRENATE:花王株式会社(商品名),化合物名:2-环己基丙酸乙酯
5)果香酯(FRUITATE):花王株式会社(商品名),化合物名:三环[5.2.1.02,6]癸烷-2-羧酸乙酯
6)铃兰醛:Givaudan公司(商品名),化合物名:对叔丁基-α-甲基氢化肉桂醛
7)琥珀芯(AMBERCORE):花王株式会社(商品名),化合物名:1-(2-叔丁基环己氧基)-2-丁醇
8)50%IPM:表示50%肉豆蔻酸异丙酯(IPM)溶液
9)降龙涎香醚:花王株式会社(商品名),化合物名:十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃
10)DPG:二丙二醇
[表6]
比较例5 | 华丽的白花般 |
实施例3 | 有水嫩的新鲜感和清洁感的华丽的香味 |
比较例6 | 花香感弱,没有发现效果 |
比较例7 | 花香感弱,没有发现效果 |
比较例8 | 有花香感,但是水嫩感不足 |
如上述表6所示,可以确认本发明的衣料用液体洗涤剂用香料组合物可以得到有清洁感的水嫩的花香调。
在具有表7记载的组成的液体洗涤剂组合物99.5质量份中配合表5记载的实施例3的香料组合物0.5质量份,得到衣料用液体洗涤剂组合物。将其称量20g,溶解于30L水中。在该水溶液中放入棉毛巾2kg,进行洗涤处理5分钟,漂洗1分钟后进行脱水。评价该棉毛巾的气味。同样地对于比较例5~8也评价脱水后的气味。将感官评价的结果示于表8中。
[表7]
配合成分 | 质量% |
烷基(C12~C14)O(EO)7(PO)2(EO)3H | 35 |
直链烷基(C10~C18)苯磺酸钠 | 1 |
脂肪酸(月桂酸、肉豆蔻酸) | 1 |
单乙醇胺 | 5 |
亚硫酸钠 | 0.1 |
乙醇 | 2 |
酶 | 0.5 |
水 | 余量 |
合计 | 99.5 |
[表8]
比较例5 | 华丽的花香味 |
实施例3 | 与比较例5相比更水嫩,自然的花香味 |
比较例6 | 花香感弱,与对照(比较例5)相比没变化16 --> |
比较例7 | 花香感弱,与对照(比较例5)相比没变化 |
比较例8 | 对照(比较例5)的花香感稍微变强 |
如上述表8所示,可以确认本发明的液体洗涤剂组合物扩散性高变得水嫩,由此带来有清洁感的自然的花香味。
产业上利用的可能性
本发明的香料组合物由于含有4,7-二甲基辛烷-3-醇(化合物(I)),因此,可以作为强烈具有水嫩花香调的香料原材料使用。另外,本发明的4,7-二甲基辛烷-3-醇由于平衡性良好地具有花般的香气和柑橘·绿香的香气,因此,可以单独或与其它成分组合而作为毛发化妆品和柔软剂等的盥洗产品的赋香成分使用。
Claims (11)
1.一种香料组合物,其中,
含有4,7-二甲基辛烷-3-醇。
2.如权利要求1所述的香料组合物,其中,
进一步含有选自4,7-二甲基辛烷-3-醇以外的醇类、酯类、碳酸酯类、醛类、酮类、醚类以及内酯类中的1种以上。
3.如权利要求1或2所述的香料组合物,其中,
进一步含有油剂。
4.如权利要求1~3中任一项所述的香料组合物,其中,
进一步含有表面活性剂。
5.一种纤维处理组合物,其中,
含有权利要求1~4中任一项所述的香料组合物。
6.一种柔软剂,其中,
含有权利要求1~4中任一项所述的香料组合物。
7.一种化妆品,其中,
含有权利要求1~4中任一项所述的香料组合物。
8.一种清洁剂组合物,其中,
含有权利要求1~4中任一项所述的香料组合物。
9.一种将4,7-二甲基辛烷-3-醇作为赋香成分使用的方法。
10.一种4,7-二甲基辛烷-3-醇的制造方法,其中,
包括使用异戊醛和3-戊酮进行交叉羟醛加成反应,接着进行脱水、还原,得到4,7-二甲基辛烷-3-醇的工序。
11.4,7-二甲基辛烷-3-醇。
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CN106517707A (zh) * | 2016-12-15 | 2017-03-22 | 佛山慧创正元新材料科技有限公司 | 一种新型污泥除臭液 |
CN110187033A (zh) * | 2019-06-14 | 2019-08-30 | 江西省药品检验检测研究院 | 新铃兰醛的制备方法及其在化妆品检测中的用途 |
CN110183319A (zh) * | 2019-06-14 | 2019-08-30 | 江西省药品检验检测研究院 | 制备化妆品检测用新铃兰醛的方法 |
CN112569393A (zh) * | 2019-09-27 | 2021-03-30 | 广州汽车集团股份有限公司 | 一种车用香氛及其制备方法 |
CN113226030A (zh) * | 2018-12-28 | 2021-08-06 | 花王株式会社 | 害虫驱避组合物 |
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JP7028552B2 (ja) | 2016-11-24 | 2022-03-02 | 花王株式会社 | 温熱具 |
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CN110187033A (zh) * | 2019-06-14 | 2019-08-30 | 江西省药品检验检测研究院 | 新铃兰醛的制备方法及其在化妆品检测中的用途 |
CN110183319A (zh) * | 2019-06-14 | 2019-08-30 | 江西省药品检验检测研究院 | 制备化妆品检测用新铃兰醛的方法 |
CN110187033B (zh) * | 2019-06-14 | 2021-09-17 | 江西省药品检验检测研究院 | 新铃兰醛的制备方法及其在化妆品检测中的用途 |
CN110183319B (zh) * | 2019-06-14 | 2021-11-09 | 江西省药品检验检测研究院 | 制备化妆品检测用新铃兰醛的方法 |
CN112569393A (zh) * | 2019-09-27 | 2021-03-30 | 广州汽车集团股份有限公司 | 一种车用香氛及其制备方法 |
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EP3075822B1 (en) | 2019-02-27 |
WO2015079798A1 (ja) | 2015-06-04 |
US20160376521A1 (en) | 2016-12-29 |
EP3075822A1 (en) | 2016-10-05 |
JP5709969B1 (ja) | 2015-04-30 |
EP3075822A4 (en) | 2017-05-17 |
JP2015105327A (ja) | 2015-06-08 |
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