ES2451521T3 - Nuevos dioxanos bicíclicos, su preparación y uso como compuestos fragantes - Google Patents
Nuevos dioxanos bicíclicos, su preparación y uso como compuestos fragantes Download PDFInfo
- Publication number
- ES2451521T3 ES2451521T3 ES10745409.2T ES10745409T ES2451521T3 ES 2451521 T3 ES2451521 T3 ES 2451521T3 ES 10745409 T ES10745409 T ES 10745409T ES 2451521 T3 ES2451521 T3 ES 2451521T3
- Authority
- ES
- Spain
- Prior art keywords
- dioxin
- group
- methyl
- butyl
- benzo
- 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.)
- Active
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 92
- -1 bicyclic dioxanes Chemical class 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 15
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 15
- 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 abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 89
- 239000003205 fragrance Substances 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 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
- 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
- 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 230
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 59
- 238000005160 1H NMR spectroscopy Methods 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 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
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 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 18
- 239000012230 colorless oil Substances 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 17
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 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 12
- IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 12
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 125000005594 diketone group Chemical group 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 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 9
- 239000006071 cream Substances 0.000 description 9
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 7
- 239000005770 Eugenol Substances 0.000 description 7
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 7
- 229960002217 eugenol Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- 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
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 240000007185 Albizia julibrissin Species 0.000 description 5
- 235000011468 Albizia julibrissin Nutrition 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
- 239000002781 deodorant agent Substances 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 4
- 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
- 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
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 4
- 240000003538 Chamaemelum nobile Species 0.000 description 4
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 4
- 239000005792 Geraniol Substances 0.000 description 4
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 4
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-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
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-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
- 235000013399 edible fruits Nutrition 0.000 description 4
- 150000002081 enamines Chemical class 0.000 description 4
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 4
- 229940113087 geraniol Drugs 0.000 description 4
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229940041616 menthol Drugs 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
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 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
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- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
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- 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 3
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- 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 3
- 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 3
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
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- 230000001166 anti-perspirative effect Effects 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- 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
- 208000031513 cyst Diseases 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects 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
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 235000009606 lavandin Nutrition 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- HRGPYCVTDOECMG-RHBQXOTJSA-N methyl cedryl ether Chemical compound C1[C@@]23[C@H](C)CC[C@H]2C(C)(C)[C@]1([H])[C@@](OC)(C)CC3 HRGPYCVTDOECMG-RHBQXOTJSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 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
- 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
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09305713 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| ES2451521T3 true ES2451521T3 (es) | 2014-03-27 |
Family
ID=41350300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10745409.2T Active ES2451521T3 (es) | 2009-07-29 | 2010-07-28 | Nuevos dioxanos bicíclicos, su preparación y uso como compuestos fragantes |
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 |
| PL2459546T3 (pl) | 2014-05-30 |
| JP5717740B2 (ja) | 2015-05-13 |
| BR112012008069B1 (pt) | 2020-12-01 |
| RU2012107548A (ru) | 2013-09-10 |
| DK2459546T3 (en) | 2014-03-24 |
| 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 |
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