DK2459546T3 - New bicyclic dioxanes, their preparation and their use as fragrance compounds - Google Patents
New bicyclic dioxanes, their preparation and their use as fragrance compounds Download PDFInfo
- Publication number
- DK2459546T3 DK2459546T3 DK10745409.2T DK10745409T DK2459546T3 DK 2459546 T3 DK2459546 T3 DK 2459546T3 DK 10745409 T DK10745409 T DK 10745409T DK 2459546 T3 DK2459546 T3 DK 2459546T3
- Authority
- DK
- Denmark
- Prior art keywords
- dioxin
- methyl
- group
- butyl
- benzo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 87
- -1 bicyclic dioxanes Chemical class 0.000 title claims description 38
- 239000003205 fragrance Substances 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title description 46
- 239000000203 mixture Substances 0.000 claims description 71
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000002304 perfume Substances 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000000873 masking effect Effects 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- TWSIYGATPWEKBK-UHFFFAOYSA-N 4h-1,3-benzodioxine Chemical compound C1=CC=C2OCOCC2=C1 TWSIYGATPWEKBK-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 1
- 235000019645 odor Nutrition 0.000 claims 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 59
- 238000005160 1H NMR spectroscopy Methods 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 41
- 239000003921 oil Substances 0.000 description 38
- 235000019198 oils Nutrition 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 235000013350 formula milk Nutrition 0.000 description 26
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 24
- 150000002009 diols Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 125000005594 diketone group Chemical group 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 229940086542 triethylamine Drugs 0.000 description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
- IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 9
- 239000006071 cream Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 6
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- MNBLGXDUGKWAQZ-UHFFFAOYSA-N 2-benzyl-4-methyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C2CCCCC2C(C)OC1CC1=CC=CC=C1 MNBLGXDUGKWAQZ-UHFFFAOYSA-N 0.000 description 5
- 150000001241 acetals Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- CBAWGSXVHCATED-UHFFFAOYSA-N 2-(1-hydroxy-3-methylbutyl)cyclohexan-1-ol Chemical compound CC(C)CC(O)C1CCCCC1O CBAWGSXVHCATED-UHFFFAOYSA-N 0.000 description 4
- IRORBXUOUURXRE-UHFFFAOYSA-N 2-(1-hydroxypropyl)cyclohexan-1-ol Chemical compound CCC(O)C1CCCCC1O IRORBXUOUURXRE-UHFFFAOYSA-N 0.000 description 4
- XXDOKDGDIMZUJO-UHFFFAOYSA-N 2-(3-methylbutanoyl)cyclohexan-1-one Chemical compound CC(C)CC(=O)C1CCCCC1=O XXDOKDGDIMZUJO-UHFFFAOYSA-N 0.000 description 4
- CJBGXBKIDRIJOB-UHFFFAOYSA-N 2-[hydroxy(phenyl)methyl]cyclohexan-1-ol Chemical compound C=1C=CC=CC=1C(O)C1CCCCC1O CJBGXBKIDRIJOB-UHFFFAOYSA-N 0.000 description 4
- OEKATORRSPXJHE-UHFFFAOYSA-N 2-acetylcyclohexan-1-one Chemical compound CC(=O)C1CCCCC1=O OEKATORRSPXJHE-UHFFFAOYSA-N 0.000 description 4
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 description 4
- PFDJPXDSJBDMCC-UHFFFAOYSA-N 2-propanoylcyclohexan-1-one Chemical compound CCC(=O)C1CCCCC1=O PFDJPXDSJBDMCC-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 150000002081 enamines Chemical class 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LUJIIJHOLKLWDV-UHFFFAOYSA-N 2-methyl-4-(2-methylpropyl)-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2C(CC(C)C)OC(C)OC21 LUJIIJHOLKLWDV-UHFFFAOYSA-N 0.000 description 3
- 240000007185 Albizia julibrissin Species 0.000 description 3
- 235000011468 Albizia julibrissin Nutrition 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 230000001166 anti-perspirative effect Effects 0.000 description 3
- 239000003213 antiperspirant Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 230000001815 facial effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 2
- JEPWTUCYPWOCQV-UHFFFAOYSA-N 2,4-dimethyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-dioxolane Chemical compound O1C(C)COC1(C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 JEPWTUCYPWOCQV-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- DASQRZJTRKBKPP-UHFFFAOYSA-N 5-butan-2-yl-2-(2,4-dimethylcyclohex-3-en-1-yl)-5-methyl-1,3-dioxane Chemical compound O1CC(C(C)CC)(C)COC1C1C(C)C=C(C)CC1 DASQRZJTRKBKPP-UHFFFAOYSA-N 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
- 244000068485 Convallaria majalis Species 0.000 description 2
- 235000009046 Convallaria majalis Nutrition 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 241000219995 Wisteria Species 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 229960002217 eugenol Drugs 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000008447 perception Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 150000000093 1,3-dioxanes Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- ZZFIZJDJJFYNMR-UHFFFAOYSA-N 2,2,4-trimethyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2C(C)OC(C)(C)OC21 ZZFIZJDJJFYNMR-UHFFFAOYSA-N 0.000 description 1
- ZGXLGRJFLOTNHC-UHFFFAOYSA-N 2,2-dimethyl-4-phenyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C(C)(C)OC2CCCCC2C1C1=CC=CC=C1 ZGXLGRJFLOTNHC-UHFFFAOYSA-N 0.000 description 1
- HGQHDKLBSQZULP-UHFFFAOYSA-N 2,4,6,6-tetramethyl-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine Chemical compound C1C(C)(C)CCC2OC(C)OC(C)C21 HGQHDKLBSQZULP-UHFFFAOYSA-N 0.000 description 1
- SHWFPOIJJLMZKA-UHFFFAOYSA-N 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine Chemical group C1=CC=C2C3OC(C)OC(C)C3CC2=C1 SHWFPOIJJLMZKA-UHFFFAOYSA-N 0.000 description 1
- WZHBJJGKBBVLMF-UHFFFAOYSA-N 2,4-dimethyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2OC(C)OC(C)C21 WZHBJJGKBBVLMF-UHFFFAOYSA-N 0.000 description 1
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 1
- XQUKUUQTEIJCCF-UHFFFAOYSA-N 2,4-diphenyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2C1OC(C=1C=CC=CC=1)OC2C1=CC=CC=C1 XQUKUUQTEIJCCF-UHFFFAOYSA-N 0.000 description 1
- ASONTZHSRSCEOJ-UHFFFAOYSA-N 2-(1-hydroxyethyl)-4,4-dimethylcyclohexan-1-ol Chemical compound CC(O)C1CC(C)(C)CCC1O ASONTZHSRSCEOJ-UHFFFAOYSA-N 0.000 description 1
- MVYIQVQYQBTWRR-UHFFFAOYSA-N 2-(1-hydroxyethyl)cyclohexan-1-ol Chemical compound CC(O)C1CCCCC1O MVYIQVQYQBTWRR-UHFFFAOYSA-N 0.000 description 1
- ZVLLAZFFOOZKQC-UHFFFAOYSA-N 2-(1-hydroxypropyl)-4,4-dimethylcyclohexan-1-ol Chemical compound CCC(O)C1CC(C)(C)CCC1O ZVLLAZFFOOZKQC-UHFFFAOYSA-N 0.000 description 1
- DXHVVVQSAVSHRB-UHFFFAOYSA-N 2-(2,4-dimethylcyclohex-3-en-1-yl)-4-methyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C2CCCCC2C(C)OC1C1CCC(C)=CC1C DXHVVVQSAVSHRB-UHFFFAOYSA-N 0.000 description 1
- WKFJEERVXCIQBM-UHFFFAOYSA-N 2-acetyl-4,4-dimethylcyclohexan-1-one Chemical compound CC(=O)C1CC(C)(C)CCC1=O WKFJEERVXCIQBM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- NTMBOGNIHMODLZ-UHFFFAOYSA-N 2-butyl-2,4-dimethyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2OC(CCCC)(C)OC(C)C21 NTMBOGNIHMODLZ-UHFFFAOYSA-N 0.000 description 1
- GUTOMDCBWXPRJO-UHFFFAOYSA-N 2-ethyl-4-methyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2OC(CC)OC(C)C21 GUTOMDCBWXPRJO-UHFFFAOYSA-N 0.000 description 1
- PWQYDSFEBSBKGO-UHFFFAOYSA-N 2-methyl-4-phenyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C(C)OC2CCCCC2C1C1=CC=CC=C1 PWQYDSFEBSBKGO-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- ZXJGOLMRNGHJCU-UHFFFAOYSA-N 4,4-dimethyl-2-propanoylcyclohexan-1-one Chemical compound CCC(=O)C1CC(C)(C)CCC1=O ZXJGOLMRNGHJCU-UHFFFAOYSA-N 0.000 description 1
- PXQMSTLNSHMSJB-UHFFFAOYSA-N 4,4-dimethylcyclohexan-1-one Chemical compound CC1(C)CCC(=O)CC1 PXQMSTLNSHMSJB-UHFFFAOYSA-N 0.000 description 1
- OLOGTUJODZYHCO-AATRIKPKSA-N 4,6,6-trimethyl-2-[(e)-prop-1-enyl]-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine Chemical compound C1C(C)(C)CCC2OC(/C=C/C)OC(C)C21 OLOGTUJODZYHCO-AATRIKPKSA-N 0.000 description 1
- KGWNHIBAVCUIHP-UHFFFAOYSA-N 4-(4,4-dimethylcyclohexen-1-yl)morpholine Chemical compound C1C(C)(C)CCC(N2CCOCC2)=C1 KGWNHIBAVCUIHP-UHFFFAOYSA-N 0.000 description 1
- CFLBVNHHOOZJGH-UHFFFAOYSA-N 4-(4-tert-butylcyclohexen-1-yl)morpholine Chemical compound C1C(C(C)(C)C)CCC(N2CCOCC2)=C1 CFLBVNHHOOZJGH-UHFFFAOYSA-N 0.000 description 1
- AZBGFRYNMGRDCB-UHFFFAOYSA-N 4-ethyl-2,2-dimethyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2C(CC)OC(C)(C)OC21 AZBGFRYNMGRDCB-UHFFFAOYSA-N 0.000 description 1
- ZYKVJTJNRWQRGG-UHFFFAOYSA-N 4-ethyl-2-methyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2C(CC)OC(C)OC21 ZYKVJTJNRWQRGG-UHFFFAOYSA-N 0.000 description 1
- UQCUZUJGWFZECZ-UHFFFAOYSA-N 4-ethyl-2-propan-2-yl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2C(CC)OC(C(C)C)OC21 UQCUZUJGWFZECZ-UHFFFAOYSA-N 0.000 description 1
- VGBBHJFPJMUSFO-UHFFFAOYSA-N 4-ethyl-6,6-dimethyl-2-propan-2-yl-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine Chemical compound C1CC(C)(C)CC2C(CC)OC(C(C)C)OC21 VGBBHJFPJMUSFO-UHFFFAOYSA-N 0.000 description 1
- ZOEKGDLNDKFLRB-UHFFFAOYSA-N 4-methyl-2-pentyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2OC(CCCCC)OC(C)C21 ZOEKGDLNDKFLRB-UHFFFAOYSA-N 0.000 description 1
- XCSPDVFOIFMQAK-UHFFFAOYSA-N 4-methyl-2-phenyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C2CCCCC2C(C)OC1C1=CC=CC=C1 XCSPDVFOIFMQAK-UHFFFAOYSA-N 0.000 description 1
- VKVIBBVQBYUFQL-UHFFFAOYSA-N 4-methyl-2-prop-1-enyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]dioxine Chemical compound CC1OC(OC2C1CCCC2)C=CC VKVIBBVQBYUFQL-UHFFFAOYSA-N 0.000 description 1
- RDHNTAXPFZIMDN-UHFFFAOYSA-N 6,6-Dimethoxy-2,5,5-trimethyl-2-hexene Chemical compound COC(OC)C(C)(C)CC=C(C)C RDHNTAXPFZIMDN-UHFFFAOYSA-N 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000003092 Artemisia dracunculus Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 240000009226 Corylus americana Species 0.000 description 1
- 235000001543 Corylus americana Nutrition 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241000209490 Nymphaea Species 0.000 description 1
- 235000016791 Nymphaea odorata subsp odorata Nutrition 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 235000012308 Tagetes Nutrition 0.000 description 1
- 241000736851 Tagetes Species 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 240000007316 Xerochrysum bracteatum Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 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
- 235000020232 peanut Nutrition 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09305713A EP2287159A1 (en) | 2009-07-29 | 2009-07-29 | New bicyclic dioxanes, their preparation and their use as organoleptic compounds |
| PCT/IB2010/053424 WO2011013077A1 (en) | 2009-07-29 | 2010-07-28 | New bicyclic dioxanes, their preparation and their use as fragrant compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2459546T3 true DK2459546T3 (en) | 2014-03-24 |
Family
ID=41350300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10745409.2T DK2459546T3 (en) | 2009-07-29 | 2010-07-28 | New bicyclic dioxanes, their preparation and their use as fragrance compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8569518B2 (https=) |
| EP (2) | EP2287159A1 (https=) |
| JP (1) | JP5717740B2 (https=) |
| CN (1) | CN102482253B (https=) |
| BR (1) | BR112012008069B1 (https=) |
| DK (1) | DK2459546T3 (https=) |
| ES (1) | ES2451521T3 (https=) |
| MX (1) | MX2012001273A (https=) |
| PL (1) | PL2459546T3 (https=) |
| PT (1) | PT2459546E (https=) |
| RU (1) | RU2562973C2 (https=) |
| WO (1) | WO2011013077A1 (https=) |
| ZA (1) | ZA201200562B (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6713474B2 (ja) * | 2015-01-21 | 2020-06-24 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 活性揮発性カルボニル化合物の制御放出のための光解離性アセタールおよびケタール化合物 |
| CN105044261B (zh) * | 2015-07-02 | 2020-10-16 | 谱尼测试集团深圳有限公司 | 一种个人护理品中卡拉花醛的检测方法 |
| CN115340449B (zh) * | 2022-09-02 | 2024-07-26 | 常州佳德医药科技有限公司 | 一锅法制备2-乙酰基环戊酮的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935749A1 (de) * | 1979-09-05 | 1981-03-26 | Henkel KGaA, 40589 Düsseldorf | 4-methyl-2,5-dioxa-bicyclo (4.4.0) decan-3-on, dessen herstellung und verwendung als riechstoff sowie dieses enthaltende riechstoffkompositionen |
| PT1027043E (pt) * | 1996-12-10 | 2005-02-28 | Bristol Myers Squibb Co | Benzodioxole benzofurano di-hidrobenzofurano e benzodioxano como agentes melatonergicos |
| US6303798B1 (en) * | 2001-02-23 | 2001-10-16 | International Flavors & Fragrances Inc. | Methylene dioxy tetrahydroindane derivative |
| DE10225350A1 (de) * | 2002-06-07 | 2003-12-18 | Symrise Gmbh & Co Kg | Aromakompositionen mit Frischewirkung |
-
2009
- 2009-07-29 EP EP09305713A patent/EP2287159A1/en not_active Withdrawn
-
2010
- 2010-07-28 CN CN201080038412.4A patent/CN102482253B/zh active Active
- 2010-07-28 WO PCT/IB2010/053424 patent/WO2011013077A1/en not_active Ceased
- 2010-07-28 ES ES10745409.2T patent/ES2451521T3/es active Active
- 2010-07-28 PL PL10745409T patent/PL2459546T3/pl unknown
- 2010-07-28 PT PT107454092T patent/PT2459546E/pt unknown
- 2010-07-28 US US13/387,214 patent/US8569518B2/en active Active
- 2010-07-28 EP EP10745409.2A patent/EP2459546B1/en active Active
- 2010-07-28 BR BR112012008069-5A patent/BR112012008069B1/pt active IP Right Grant
- 2010-07-28 JP JP2012522325A patent/JP5717740B2/ja active Active
- 2010-07-28 RU RU2012107548/04A patent/RU2562973C2/ru active
- 2010-07-28 DK DK10745409.2T patent/DK2459546T3/en active
- 2010-07-28 MX MX2012001273A patent/MX2012001273A/es active IP Right Grant
-
2012
- 2012-01-24 ZA ZA2012/00562A patent/ZA201200562B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT2459546E (pt) | 2014-03-20 |
| US8569518B2 (en) | 2013-10-29 |
| ZA201200562B (en) | 2012-10-31 |
| ES2451521T3 (es) | 2014-03-27 |
| PL2459546T3 (pl) | 2014-05-30 |
| JP5717740B2 (ja) | 2015-05-13 |
| BR112012008069B1 (pt) | 2020-12-01 |
| RU2012107548A (ru) | 2013-09-10 |
| RU2562973C2 (ru) | 2015-09-10 |
| JP2013500327A (ja) | 2013-01-07 |
| EP2459546A1 (en) | 2012-06-06 |
| CN102482253A (zh) | 2012-05-30 |
| WO2011013077A1 (en) | 2011-02-03 |
| US20120165557A1 (en) | 2012-06-28 |
| BR112012008069A2 (pt) | 2016-03-01 |
| EP2287159A1 (en) | 2011-02-23 |
| MX2012001273A (es) | 2012-06-19 |
| EP2459546B1 (en) | 2013-12-18 |
| CN102482253B (zh) | 2014-08-06 |
| HK1169986A1 (en) | 2013-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0672952A (ja) | 新規エステル化合物、香料組成物および付香物品の匂い特性を改善、強調、付与または修正する方法、付香組成物および物品、および新規化合物を製造するための方法および中間体 | |
| JP5479466B2 (ja) | 匂い物質として適するイソロンギホラニル誘導体 | |
| KR101819615B1 (ko) | 나무 향을 지닌 화합물 | |
| DK2459546T3 (en) | New bicyclic dioxanes, their preparation and their use as fragrance compounds | |
| RU2482108C2 (ru) | Замещенные октан(ен)нитрилы, способ их получения и их применение в парфюмерии | |
| CA2969389C (en) | Novel acetals of 1-(3,3-dimethylcyclohex-1-eneyl) ethanone, method for the production thereof and use of same in perfumery | |
| JPS63264477A (ja) | 環状アセタール化合物及び前記化合物を含有する香料組成物 | |
| ES2330640T3 (es) | Derivados de 3-isopropil-1-metilciclopentilo y su utilizacion en aplicaciones de fragancia. | |
| JP2013500327A5 (https=) | ||
| HK1169986B (en) | New bicyclic dioxanes, their preparation and their use as fragrant compounds | |
| EP1515938A1 (en) | Alcohols and ketones of bi- and tricyclic compounds and odorant compositions | |
| JP4956441B2 (ja) | 新規なトリメチルシクロドデカトリエン誘導体、その使用及びそれを含有する芳香製品 | |
| HK1153475A (en) | New bicyclic dioxanes, their preparation and their use as organoleptic compounds | |
| MX2014003580A (es) | Nuevos aldehidos cicloalcanicos , su procedimiento de preparación asi como su utilizacion en perfumeria. | |
| MX2007001518A (es) | Tetrahidropiran(ona)s beta-sustituidas, procedimiento para su sintesis y su uso en perfumeria. | |
| WO2006058450A2 (en) | Dioxole tricyclic compounds and their use as fragrances | |
| EP2209389B1 (en) | Bicyclic campholenic derivatives | |
| HK1239668B (en) | Novel acetals of 1-(3,3-dimethylcyclohex-1-enyl) ethanone, method for the production thereof and use of same in perfumery | |
| HK1239668A1 (en) | Novel acetals of 1-(3,3-dimethylcyclohex-1-enyl) ethanone, method for the production thereof and use of same in perfumery |