BR112012008584B1 - Ésteres como componentes perfumantes - Google Patents
Ésteres como componentes perfumantes Download PDFInfo
- Publication number
- BR112012008584B1 BR112012008584B1 BR112012008584-0A BR112012008584A BR112012008584B1 BR 112012008584 B1 BR112012008584 B1 BR 112012008584B1 BR 112012008584 A BR112012008584 A BR 112012008584A BR 112012008584 B1 BR112012008584 B1 BR 112012008584B1
- Authority
- BR
- Brazil
- Prior art keywords
- group
- cyclopropylmethyl
- methyl
- hydrogen atom
- formula
- Prior art date
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- MHKKFRQKYWBFON-ARJAWSKDSA-N cyclopropylmethyl (z)-hex-3-enoate Chemical compound CC\C=C/CC(=O)OCC1CC1 MHKKFRQKYWBFON-ARJAWSKDSA-N 0.000 claims description 9
- 239000002304 perfume Substances 0.000 claims description 9
- -1 (E) - 2-methylhex-2-enoate Cyclopropylmethyl (3E) -3-hexenoate Chemical compound 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- GLHJGUCKQOQWDU-ARJAWSKDSA-N cyclobutylmethyl (z)-hex-3-enoate Chemical compound CC\C=C/CC(=O)OCC1CCC1 GLHJGUCKQOQWDU-ARJAWSKDSA-N 0.000 claims description 7
- BMKIEADYHVMBKO-NSCUHMNNSA-N cyclopropylmethyl (e)-hex-4-enoate Chemical compound C\C=C\CCC(=O)OCC1CC1 BMKIEADYHVMBKO-NSCUHMNNSA-N 0.000 claims description 6
- PBKRQXKJECNSJC-UHFFFAOYSA-N cyclopropylmethyl hexanoate Chemical compound CCCCCC(=O)OCC1CC1 PBKRQXKJECNSJC-UHFFFAOYSA-N 0.000 claims description 6
- WQEWYKRZAULLHT-PLNGDYQASA-N 1-cyclopropylethyl (z)-hex-3-enoate Chemical compound CC\C=C/CC(=O)OC(C)C1CC1 WQEWYKRZAULLHT-PLNGDYQASA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000002386 air freshener Substances 0.000 claims description 5
- FFWNQLIBSZWYQO-UHFFFAOYSA-N cyclopropylmethyl 2-methylhexanoate Chemical compound CCCCC(C)C(=O)OCC1CC1 FFWNQLIBSZWYQO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- XXHDAWYDNSXJQM-ARJAWSKDSA-N cis-hex-3-enoic acid Chemical compound CC\C=C/CC(O)=O XXHDAWYDNSXJQM-ARJAWSKDSA-N 0.000 claims description 4
- NEBMOJHREBKXMG-CSKARUKUSA-N cyclopropylmethyl (e)-3-methylhept-2-enoate Chemical compound CCCC\C(C)=C\C(=O)OCC1CC1 NEBMOJHREBKXMG-CSKARUKUSA-N 0.000 claims description 4
- HGPWSUBACJQZOI-SNAWJCMRSA-N cyclopropylmethyl (e)-hex-2-enoate Chemical compound CCC\C=C\C(=O)OCC1CC1 HGPWSUBACJQZOI-SNAWJCMRSA-N 0.000 claims description 4
- MHKKFRQKYWBFON-ONEGZZNKSA-N cyclopropylmethyl (e)-hex-3-enoate Chemical compound CC\C=C\CC(=O)OCC1CC1 MHKKFRQKYWBFON-ONEGZZNKSA-N 0.000 claims description 4
- GTPQEICJBDKALV-UHFFFAOYSA-N cyclopropylmethyl octanoate Chemical compound CCCCCCCC(=O)OCC1CC1 GTPQEICJBDKALV-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- AZPBKDDACJBGAQ-UHFFFAOYSA-N cyclopropylmethyl 3-cyclohexylpropanoate Chemical compound C1CC1COC(=O)CCC1CCCCC1 AZPBKDDACJBGAQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 239000002979 fabric softener Substances 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 241000195940 Bryophyta Species 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- QWOGLSLFIMJKRY-UHFFFAOYSA-N cyclopropylmethyl hexa-2,4-dienoate Chemical compound CC=CC=CC(=O)OCC1CC1 QWOGLSLFIMJKRY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000008266 hair spray Substances 0.000 claims description 2
- 235000011929 mousse Nutrition 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 239000013042 solid detergent Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 30
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 239000000306 component Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 235000019645 odor Nutrition 0.000 description 11
- 235000014443 Pyrus communis Nutrition 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XEAIHUDTEINXFG-PLNGDYQASA-N Methyl (Z)-3-hexenoate Chemical compound CC\C=C/CC(=O)OC XEAIHUDTEINXFG-PLNGDYQASA-N 0.000 description 4
- 238000005538 encapsulation Methods 0.000 description 4
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical class CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 3
- WSTQLNQRVZNEDV-CSKARUKUSA-N (e)-4-methyldec-3-en-5-ol Chemical compound CCCCCC(O)C(\C)=C\CC WSTQLNQRVZNEDV-CSKARUKUSA-N 0.000 description 3
- DKKVKJZXOBFLRY-UHFFFAOYSA-N 1-cyclopropylethanol Chemical compound CC(O)C1CC1 DKKVKJZXOBFLRY-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005888 cyclopropanation reaction Methods 0.000 description 3
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- XEAIHUDTEINXFG-UHFFFAOYSA-N methyl cis-3-hexenoate Natural products CCC=CCC(=O)OC XEAIHUDTEINXFG-UHFFFAOYSA-N 0.000 description 3
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZHHYXNZJDGDGPJ-BSWSSELBSA-N (2e,4e)-nona-2,4-dienal Chemical compound CCCC\C=C\C=C\C=O ZHHYXNZJDGDGPJ-BSWSSELBSA-N 0.000 description 2
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 description 2
- XOOYZPVBQLXRDI-RMKNXTFCSA-N 1-cyclopropylethyl (e)-2-methylhex-2-enoate Chemical compound CCC\C=C(/C)C(=O)OC(C)C1CC1 XOOYZPVBQLXRDI-RMKNXTFCSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- 241000234282 Allium Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- NEBMOJHREBKXMG-NTMALXAHSA-N cyclopropylmethyl (z)-3-methylhept-2-enoate Chemical compound CCCC\C(C)=C/C(=O)OCC1CC1 NEBMOJHREBKXMG-NTMALXAHSA-N 0.000 description 2
- XFAHCLKRWZBGHN-UHFFFAOYSA-N cyclopropylmethyl heptanoate Chemical compound CCCCCCC(=O)OCC1CC1 XFAHCLKRWZBGHN-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
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- PIZQWRXTMGASCZ-UHFFFAOYSA-N (1-methylcyclopropyl)methanol Chemical compound OCC1(C)CC1 PIZQWRXTMGASCZ-UHFFFAOYSA-N 0.000 description 1
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- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- NEBMOJHREBKXMG-UHFFFAOYSA-N cyclopropylmethyl 3-methylhept-2-enoate Chemical compound CCCCC(C)=CC(=O)OCC1CC1 NEBMOJHREBKXMG-UHFFFAOYSA-N 0.000 description 1
- LIRRPMXXEQKRRT-UHFFFAOYSA-N cyclopropylmethyl 3-methylhex-2-enoate Chemical compound CCCC(C)=CC(=O)OCC1CC1 LIRRPMXXEQKRRT-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- MHKKFRQKYWBFON-UHFFFAOYSA-N cyclopropylmethyl hex-3-enoate Chemical compound CCC=CCC(=O)OCC1CC1 MHKKFRQKYWBFON-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000001449 ethyl (2R)-2-methylpentanoate Substances 0.000 description 1
- MXSSZEHSJNPQDF-BQYQJAHWSA-N ethyl (e)-2-methylhex-2-enoate Chemical compound CCC\C=C(/C)C(=O)OCC MXSSZEHSJNPQDF-BQYQJAHWSA-N 0.000 description 1
- 229940057975 ethyl citrate Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N gamma-octalactone Chemical compound CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 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 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000416 hydrocolloid Substances 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- XEAIHUDTEINXFG-SNAWJCMRSA-N methyl (e)-hex-3-enoate Chemical compound CC\C=C\CC(=O)OC XEAIHUDTEINXFG-SNAWJCMRSA-N 0.000 description 1
- MEZYCNMPBPQTLK-ONEGZZNKSA-N methyl (e)-hex-4-enoate Chemical compound COC(=O)CC\C=C\C MEZYCNMPBPQTLK-ONEGZZNKSA-N 0.000 description 1
- ZDBCSZOFHPULAS-UHFFFAOYSA-N methyl 2-cyclopentylideneacetate Chemical compound COC(=O)C=C1CCCC1 ZDBCSZOFHPULAS-UHFFFAOYSA-N 0.000 description 1
- FTNNIIIFSINEIF-UHFFFAOYSA-N methyl 3-methylhex-2-enoate Chemical compound CCCC(C)=CC(=O)OC FTNNIIIFSINEIF-UHFFFAOYSA-N 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- NTLJTUMJJWVCTL-UHFFFAOYSA-N methyl non-2-ynoate Chemical compound CCCCCCC#CC(=O)OC NTLJTUMJJWVCTL-UHFFFAOYSA-N 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- WXETUDXXEZHSCS-MAVITOTKSA-N vertofix coeur Chemical compound C[C@@H]1CC[C@@]2(C(/CC3)=C\C(C)=O)[C@@H]3C(C)(C)[C@@H]1C2 WXETUDXXEZHSCS-MAVITOTKSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
-
- 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
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- 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
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- 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
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Beans For Foods Or Fodder (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09174999 | 2009-11-04 | ||
| EP091749994 | 2009-11-04 | ||
| PCT/IB2010/054673 WO2011055251A1 (en) | 2009-11-04 | 2010-10-15 | Esters as perfuming ingredients |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112012008584A2 BR112012008584A2 (pt) | 2016-04-05 |
| BR112012008584B1 true BR112012008584B1 (pt) | 2020-05-05 |
Family
ID=41565892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012008584-0A BR112012008584B1 (pt) | 2009-11-04 | 2010-10-15 | Ésteres como componentes perfumantes |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8871967B2 (enExample) |
| EP (1) | EP2496548B1 (enExample) |
| JP (1) | JP5689135B2 (enExample) |
| CN (1) | CN102596890B (enExample) |
| BR (1) | BR112012008584B1 (enExample) |
| ES (1) | ES2432676T3 (enExample) |
| WO (1) | WO2011055251A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6498184B2 (ja) * | 2014-04-21 | 2019-04-10 | 高砂香料工業株式会社 | 新規化合物及び該化合物を含有する香料組成物 |
| WO2019059375A1 (ja) | 2017-09-25 | 2019-03-28 | 高砂香料工業株式会社 | 香料前駆体 |
| CN113195444A (zh) * | 2018-10-02 | 2021-07-30 | 西姆莱斯股份公司 | 制备链烷二醇的方法 |
| US11111458B2 (en) * | 2018-10-10 | 2021-09-07 | International Flavors & Fragrances Inc. | Cyclopropylmethoxy derivatives |
| JP7326243B2 (ja) * | 2020-11-20 | 2023-08-15 | 長谷川香料株式会社 | シクロプロパン骨格を有するラクトン化合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008258A (en) * | 1973-04-13 | 1977-02-15 | Zoecon Corporation | Cyclopropyl methyl esters |
| EP1182190A1 (en) * | 2000-08-25 | 2002-02-27 | Givaudan SA | Unsaturated esters |
-
2010
- 2010-10-15 US US13/501,052 patent/US8871967B2/en active Active
- 2010-10-15 WO PCT/IB2010/054673 patent/WO2011055251A1/en not_active Ceased
- 2010-10-15 BR BR112012008584-0A patent/BR112012008584B1/pt active IP Right Grant
- 2010-10-15 EP EP10776166.0A patent/EP2496548B1/en active Active
- 2010-10-15 ES ES10776166T patent/ES2432676T3/es active Active
- 2010-10-15 CN CN201080049460.3A patent/CN102596890B/zh active Active
- 2010-10-15 JP JP2012537462A patent/JP5689135B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2432676T3 (es) | 2013-12-04 |
| JP5689135B2 (ja) | 2015-03-25 |
| US20120195844A1 (en) | 2012-08-02 |
| CN102596890B (zh) | 2014-12-17 |
| WO2011055251A1 (en) | 2011-05-12 |
| JP2013510134A (ja) | 2013-03-21 |
| BR112012008584A2 (pt) | 2016-04-05 |
| CN102596890A (zh) | 2012-07-18 |
| EP2496548A1 (en) | 2012-09-12 |
| US8871967B2 (en) | 2014-10-28 |
| EP2496548B1 (en) | 2013-08-28 |
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| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B06T | Formal requirements before examination [chapter 6.20 patent gazette] | ||
| B07A | Technical examination (opinion): publication of technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B06A | Notification to applicant to reply to the report for non-patentability or inadequacy of the application [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 15/10/2010, OBSERVADAS AS CONDICOES LEGAIS. |