JP2013500327A5 - - Google Patents
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- JP2013500327A5 JP2013500327A5 JP2012522325A JP2012522325A JP2013500327A5 JP 2013500327 A5 JP2013500327 A5 JP 2013500327A5 JP 2012522325 A JP2012522325 A JP 2012522325A JP 2012522325 A JP2012522325 A JP 2012522325A JP 2013500327 A5 JP2013500327 A5 JP 2013500327A5
- Authority
- JP
- Japan
- Prior art keywords
- dioxin
- methyl
- benzo
- group
- butyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 36
- 239000003205 fragrance Substances 0.000 claims description 9
- 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 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 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 claims description 5
- 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 claims description 5
- 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 claims description 5
- 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 claims description 5
- 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 claims description 4
- 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 claims 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- DQKHINHSAJSJFU-UHFFFAOYSA-N 4-methylspiro[4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine-2,1'-cyclopentane] Chemical compound O1C2CCCCC2C(C)OC21CCCC2 DQKHINHSAJSJFU-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- HAFWAVOMECONDC-UHFFFAOYSA-N 6-tert-butyl-2,4-dimethyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1C(C(C)(C)C)CCC2OC(C)OC(C)C21 HAFWAVOMECONDC-UHFFFAOYSA-N 0.000 claims description 2
- YZIWHKHXPUIDLI-UHFFFAOYSA-N 6-tert-butyl-2-methyl-4-phenyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C(C)OC2CCC(C(C)(C)C)CC2C1C1=CC=CC=C1 YZIWHKHXPUIDLI-UHFFFAOYSA-N 0.000 claims description 2
- SJOGWQIHALUVJA-UHFFFAOYSA-N 6-tert-butyl-4-ethyl-2-propan-2-yl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CC(C(C)(C)C)CC2C(CC)OC(C(C)C)OC21 SJOGWQIHALUVJA-UHFFFAOYSA-N 0.000 claims description 2
- GCXZZULDTYOHEY-UHFFFAOYSA-N CCCCCC1C2CCCCC2OC(O1)(C)C Chemical compound CCCCCC1C2CCCCC2OC(O1)(C)C GCXZZULDTYOHEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- -1 i- butyl Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 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 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 230000000873 masking effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 56
- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- 150000002009 diols Chemical class 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 239000012230 colorless oil Substances 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- 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 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- UCZQXJKDCHCTAI-UHFFFAOYSA-N 4h-1,3-dioxine Chemical compound C1OCC=CO1 UCZQXJKDCHCTAI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 240000007185 Albizia julibrissin Species 0.000 description 2
- 235000011468 Albizia julibrissin Nutrition 0.000 description 2
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 description 2
- 235000001636 Mentha x rotundifolia Nutrition 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 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
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 235000013399 edible fruits Nutrition 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
- 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
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 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
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 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 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
- 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
- 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 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
- 235000005881 Calendula officinalis Nutrition 0.000 description 1
- 241000723346 Cinnamomum camphora 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
- 244000068485 Convallaria majalis Species 0.000 description 1
- 235000009046 Convallaria majalis Nutrition 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 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
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 240000000785 Tagetes erecta Species 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 240000007316 Xerochrysum bracteatum Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 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
- 230000008447 perception Effects 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000001019 trigonella foenum-graecum Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09305713.1 | 2009-07-29 | ||
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2013500327A JP2013500327A (ja) | 2013-01-07 |
| JP2013500327A5 true JP2013500327A5 (https=) | 2015-02-12 |
| JP5717740B2 JP5717740B2 (ja) | 2015-05-13 |
Family
ID=41350300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012522325A Active JP5717740B2 (ja) | 2009-07-29 | 2010-07-28 | 新規の二環状ジオキサン類、それらの調製、及び芳香性化合物としてのそれらの使用 |
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
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