JP7027404B2 - フレグランス成分としての６－イソプロピル－２，４－ジメチルシクロヘキセン－１－オール化合物 - Google Patents
フレグランス成分としての６－イソプロピル－２，４－ジメチルシクロヘキセン－１－オール化合物 Download PDFInfo
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- JP7027404B2 JP7027404B2 JP2019503942A JP2019503942A JP7027404B2 JP 7027404 B2 JP7027404 B2 JP 7027404B2 JP 2019503942 A JP2019503942 A JP 2019503942A JP 2019503942 A JP2019503942 A JP 2019503942A JP 7027404 B2 JP7027404 B2 JP 7027404B2
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- isopropyl
- dimethylcyclohexa
- carbon
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- 239000003205 fragrance Substances 0.000 title claims description 32
- -1 6-Isopropyl-2,4-dimethylcyclohexene-1-ol compound Chemical class 0.000 title description 20
- 239000000203 mixture Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 32
- SFCVUROYEXWUIY-UHFFFAOYSA-N 2,4-dimethyl-6-propan-2-ylcyclohex-3-en-1-ol Chemical compound C(C)(C)C1CC(=CC(C1O)C)C SFCVUROYEXWUIY-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- UHELJNANGXRBDI-UHFFFAOYSA-N 2,4,7-trimethyloct-6-en-1-ol Chemical compound CC(CO)CC(CC=C(C)C)C UHELJNANGXRBDI-UHFFFAOYSA-N 0.000 claims description 2
- KHCFXIFUQOTASV-UHFFFAOYSA-N 2,4,7-trimethyloctan-1-ol Chemical compound CC(CO)CC(CCC(C)C)C KHCFXIFUQOTASV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- FQVDHDCVQRIODU-UHFFFAOYSA-N 2,4,7-trimethylocta-2,6-diene Chemical compound CC(C)=CC(C)CC=C(C)C FQVDHDCVQRIODU-UHFFFAOYSA-N 0.000 claims 1
- SGSXZFVSRQWNEP-UHFFFAOYSA-N 4,6-dimethyl-2-propan-2-ylcyclohex-3-en-1-ol Chemical compound C(C)(C)C1C=C(CC(C1O)C)C SGSXZFVSRQWNEP-UHFFFAOYSA-N 0.000 claims 1
- WNHPULBFSIXBBG-UHFFFAOYSA-N CC(CO)C=C(CC=C(C)C)C Chemical compound CC(CO)C=C(CC=C(C)C)C WNHPULBFSIXBBG-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 46
- 235000019645 odor Nutrition 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002304 perfume Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000002537 cosmetic Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-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
- 239000003599 detergent Substances 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 239000000341 volatile oil Substances 0.000 description 4
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 3
- LRLHUGKKNIXVGY-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enoxymethoxy)but-2-ene Chemical compound CC(C)=CCOCOCC=C(C)C LRLHUGKKNIXVGY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 3
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 3
- DCLJJQVXUIZINW-UHFFFAOYSA-N (2,4-dimethyl-6-propan-2-ylcyclohex-3-en-1-yl)methanol Chemical compound C(C)(C)C1CC(=CC(C1CO)C)C DCLJJQVXUIZINW-UHFFFAOYSA-N 0.000 description 2
- CRDAMVZIKSXKFV-GNESMGCMSA-N (2-trans,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C\CO CRDAMVZIKSXKFV-GNESMGCMSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- 239000001147 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran Substances 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N (E)-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- 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 2
- RNLHVODSMDJCBR-SOFGYWHQSA-N (e)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C\C1CC=C(C)C1(C)C RNLHVODSMDJCBR-SOFGYWHQSA-N 0.000 description 2
- NEHPIUGJDUWSRR-UHFFFAOYSA-N 1-(4-propan-2-ylcyclohexyl)ethanol Chemical compound CC(C)C1CCC(C(C)O)CC1 NEHPIUGJDUWSRR-UHFFFAOYSA-N 0.000 description 2
- FYMOBFDUZIDKMI-UHFFFAOYSA-N 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol Chemical compound CC1=CC=CC(CC(C)(C)CO)=C1 FYMOBFDUZIDKMI-UHFFFAOYSA-N 0.000 description 2
- BJTIVTZNXHDDIQ-UHFFFAOYSA-N 2,4-dimethyl-6-propan-2-ylcyclohexen-1-ol Chemical class C(C)(C)C1CC(CC(=C1O)C)C BJTIVTZNXHDDIQ-UHFFFAOYSA-N 0.000 description 2
- WKHTUDYDJUHYMK-UHFFFAOYSA-N 2-cyclododecylpropan-1-ol Chemical compound OCC(C)C1CCCCCCCCCCC1 WKHTUDYDJUHYMK-UHFFFAOYSA-N 0.000 description 2
- YLIXVKUWWOQREC-UHFFFAOYSA-N 2-methyl-3-[4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CC(C)C=O)C=C1 YLIXVKUWWOQREC-UHFFFAOYSA-N 0.000 description 2
- ZJPKYCLAROITRY-UHFFFAOYSA-N 3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene Chemical compound CCOC(C)OC(C)(C=C)CCC=C(C)C ZJPKYCLAROITRY-UHFFFAOYSA-N 0.000 description 2
- OHRBQTOZYGEWCJ-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=CC(C(C)CC=O)=C1 OHRBQTOZYGEWCJ-UHFFFAOYSA-N 0.000 description 2
- VSIXJPFQJMODCS-UHFFFAOYSA-N 3-methyl-4-phenylbutan-2-ol Chemical compound CC(O)C(C)CC1=CC=CC=C1 VSIXJPFQJMODCS-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
- ABRIMXGLNHCLIP-VURMDHGXSA-N 5-Cyclohexadecenone Chemical compound O=C1CCCCCCCCCC\C=C/CCC1 ABRIMXGLNHCLIP-VURMDHGXSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
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- 150000002596 lactones Chemical class 0.000 description 2
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 2
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- 239000012044 organic layer Substances 0.000 description 2
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- 229910052760 oxygen Inorganic materials 0.000 description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
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- 239000000499 gel Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 229940089454 lauryl aldehyde Drugs 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 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
- IPWBXORAIBJDDQ-UHFFFAOYSA-N methyl 2-hexyl-3-oxocyclopentane-1-carboxylate Chemical compound CCCCCCC1C(C(=O)OC)CCC1=O IPWBXORAIBJDDQ-UHFFFAOYSA-N 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 229930014626 natural product Natural products 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
- SHPVOXFREBUEHB-UHFFFAOYSA-N oct-6-en-1-ol Chemical compound CC=CCCCCCO SHPVOXFREBUEHB-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012438 synthetic essential oil Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
- C07C35/08—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 six-membered rings
- C07C35/18—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 six-membered rings with unsaturation at least in the ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- 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
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1613013.0A GB201613013D0 (en) | 2016-07-27 | 2016-07-27 | Organic compound |
| GB1613013.0 | 2016-07-27 | ||
| PCT/EP2017/068999 WO2018019935A1 (en) | 2016-07-27 | 2017-07-27 | 6-isopropyl-2,4-dimethylcyclohexen-1-ol compounds as fragrance ingredients |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019523267A JP2019523267A (ja) | 2019-08-22 |
| JP2019523267A5 JP2019523267A5 (enExample) | 2020-08-13 |
| JP7027404B2 true JP7027404B2 (ja) | 2022-03-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019503942A Active JP7027404B2 (ja) | 2016-07-27 | 2017-07-27 | フレグランス成分としての６－イソプロピル－２，４－ジメチルシクロヘキセン－１－オール化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10800722B2 (enExample) |
| EP (1) | EP3490966B1 (enExample) |
| JP (1) | JP7027404B2 (enExample) |
| CN (1) | CN109476570B (enExample) |
| BR (1) | BR112019000543B1 (enExample) |
| GB (1) | GB201613013D0 (enExample) |
| MX (1) | MX2019000127A (enExample) |
| SG (1) | SG11201900016SA (enExample) |
| WO (1) | WO2018019935A1 (enExample) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010015965A2 (en) | 2008-08-04 | 2010-02-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Methods and compositions for treating neuronal damage and modulating transient receptor potential channels |
| JP2016500666A (ja) | 2012-10-05 | 2016-01-14 | ヴェ マン フィユＶ． Ｍａｎｅ Ｆｉｌｓ | シクロヘキセノンの合成方法および香料製造におけるその使用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4326997A (en) * | 1980-10-08 | 1982-04-27 | Fritzsche Dodge & Olcott Inc. | Fragrance compositions of alicyclic ketone and alcohol derivatives |
| EP0079989A1 (en) * | 1981-11-23 | 1983-06-01 | Fritzsche Dodge & Olcott Inc. | Alicyclic ketone and alcohol derivatives |
| JPS58144334A (ja) * | 1982-02-12 | 1983-08-27 | フリツエ・ダツジ・アンド・オルコツト・インコ−ポレイテイド | 脂環式アルコール誘導体 |
| DE69203575T2 (de) | 1991-11-25 | 1996-01-18 | Firmenich & Cie | Tertiäre cyclische Alkohole und ihre Anwendung als Riechstoffbestandteile. |
| DE60014639T2 (de) | 1999-06-28 | 2005-05-25 | Quest International B.V. | Riechstoffe |
| EP1213276A1 (en) * | 2000-12-05 | 2002-06-12 | Givaudan SA | Substituted cyclohexenes |
| GB0624814D0 (en) * | 2006-12-13 | 2007-01-24 | Givaudan Sa | Organic compounds |
| GB0715496D0 (en) * | 2007-08-10 | 2007-09-19 | Givauden Sa | Novel process |
| FR2959738B1 (fr) | 2010-05-05 | 2012-05-11 | Mane Fils V | Composes a la note boisee. |
| CN107012022A (zh) * | 2010-06-22 | 2017-08-04 | 宝洁公司 | 香料体系 |
| GB201013474D0 (en) * | 2010-08-11 | 2010-09-22 | Givaudan Sa | Organic compounds |
| CN103562167B (zh) * | 2011-05-25 | 2015-07-29 | 奇华顿股份有限公司 | 用于香料组合物和香味产品的萜烯醇 |
| US20160272612A1 (en) | 2015-03-18 | 2016-09-22 | The Regents Of The University Of California | Anthropod repellent chemicals |
-
2016
- 2016-07-27 GB GBGB1613013.0A patent/GB201613013D0/en not_active Ceased
-
2017
- 2017-07-27 US US16/318,171 patent/US10800722B2/en active Active
- 2017-07-27 CN CN201780045336.1A patent/CN109476570B/zh active Active
- 2017-07-27 WO PCT/EP2017/068999 patent/WO2018019935A1/en not_active Ceased
- 2017-07-27 JP JP2019503942A patent/JP7027404B2/ja active Active
- 2017-07-27 MX MX2019000127A patent/MX2019000127A/es unknown
- 2017-07-27 BR BR112019000543-9A patent/BR112019000543B1/pt active IP Right Grant
- 2017-07-27 SG SG11201900016SA patent/SG11201900016SA/en unknown
- 2017-07-27 EP EP17746071.4A patent/EP3490966B1/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010015965A2 (en) | 2008-08-04 | 2010-02-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Methods and compositions for treating neuronal damage and modulating transient receptor potential channels |
| JP2016500666A (ja) | 2012-10-05 | 2016-01-14 | ヴェ マン フィユＶ． Ｍａｎｅ Ｆｉｌｓ | シクロヘキセノンの合成方法および香料製造におけるその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2018019935A1 (en) | 2018-02-01 |
| GB201613013D0 (en) | 2016-09-07 |
| MX2019000127A (es) | 2019-04-01 |
| CN109476570A (zh) | 2019-03-15 |
| JP2019523267A (ja) | 2019-08-22 |
| CN109476570B (zh) | 2022-06-07 |
| BR112019000543B1 (pt) | 2022-08-09 |
| US20190233357A1 (en) | 2019-08-01 |
| EP3490966A1 (en) | 2019-06-05 |
| SG11201900016SA (en) | 2019-02-27 |
| BR112019000543A2 (pt) | 2019-04-24 |
| US10800722B2 (en) | 2020-10-13 |
| EP3490966B1 (en) | 2020-09-16 |
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