JP2008528451A - 2−c置換プロパン−1,3−ジカルボニル化合物および悪臭中和におけるその使用 - Google Patents
2−c置換プロパン−1,3−ジカルボニル化合物および悪臭中和におけるその使用 Download PDFInfo
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- JP2008528451A JP2008528451A JP2007551527A JP2007551527A JP2008528451A JP 2008528451 A JP2008528451 A JP 2008528451A JP 2007551527 A JP2007551527 A JP 2007551527A JP 2007551527 A JP2007551527 A JP 2007551527A JP 2008528451 A JP2008528451 A JP 2008528451A
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- ester
- ethyl
- hydrocarbon residue
- acetyl
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- -1 propane-1,3-dicarbonyl compounds Chemical class 0.000 title claims description 77
- 238000006386 neutralization reaction Methods 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 239000000460 chlorine Substances 0.000 claims description 45
- 229910052794 bromium Inorganic materials 0.000 claims description 44
- 229910052801 chlorine Inorganic materials 0.000 claims description 44
- 125000005842 heteroatom Chemical group 0.000 claims description 44
- 229910052710 silicon Inorganic materials 0.000 claims description 44
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 125000004185 ester group Chemical group 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 32
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 32
- 239000010703 silicon Substances 0.000 claims description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 20
- 125000001033 ether group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 claims description 6
- 235000010357 aspartame Nutrition 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003136 n-heptyl 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])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- UJLZHPXERCRUAA-UHFFFAOYSA-N diethyl 2-butanoylbut-2-enedioate Chemical compound CCCC(=O)C(C(=O)OCC)=CC(=O)OCC UJLZHPXERCRUAA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- WZQPCWQUUMNLBF-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-acetyldec-2-enoate Chemical compound CCCCCCCC=C(C(C)=O)C(=O)OCCOCCOC WZQPCWQUUMNLBF-UHFFFAOYSA-N 0.000 claims description 3
- VPNLWAHMLQRTKB-UHFFFAOYSA-N 4-o-ethyl 1-o-(2-methoxyethyl) 2-acetylbut-2-enedioate Chemical compound CCOC(=O)C=C(C(C)=O)C(=O)OCCOC VPNLWAHMLQRTKB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- CMKNNYLWGWYZGD-UHFFFAOYSA-N dibenzyl 2-octylidenepropanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(=CCCCCCCC)C(=O)OCC1=CC=CC=C1 CMKNNYLWGWYZGD-UHFFFAOYSA-N 0.000 claims description 3
- CZBMCQVEYULJOE-UHFFFAOYSA-N diethyl 2-benzoyl-3-ethoxybutanedioate Chemical compound CCOC(=O)C(OCC)C(C(=O)OCC)C(=O)C1=CC=CC=C1 CZBMCQVEYULJOE-UHFFFAOYSA-N 0.000 claims description 3
- YMUBTSFQIVTHJU-UHFFFAOYSA-N diethyl 2-benzoyl-3-hydroxybutanedioate Chemical compound CCOC(=O)C(O)C(C(=O)OCC)C(=O)C1=CC=CC=C1 YMUBTSFQIVTHJU-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- TZBUSAJVQQGGFP-UHFFFAOYSA-N ethyl 2-acetyl-5,9-dimethyldeca-2,8-dienoate Chemical compound CCOC(=O)C(C(C)=O)=CCC(C)CCC=C(C)C TZBUSAJVQQGGFP-UHFFFAOYSA-N 0.000 claims description 3
- BKULVIZFOHJLLV-UHFFFAOYSA-N ethyl 2-benzoyldec-2-enoate Chemical compound CCCCCCCC=C(C(=O)OCC)C(=O)C1=CC=CC=C1 BKULVIZFOHJLLV-UHFFFAOYSA-N 0.000 claims description 3
- FFPHIZSVBKYWOQ-UHFFFAOYSA-N ethyl 3-(4-methylcyclohexanecarbonyl)-4-oxopent-2-enoate Chemical compound CCOC(=O)C=C(C(C)=O)C(=O)C1CCC(C)CC1 FFPHIZSVBKYWOQ-UHFFFAOYSA-N 0.000 claims description 3
- PIMSKFUWNYECEL-UHFFFAOYSA-N ethyl 3-(cyclohexanecarbonyl)-4-oxopent-2-enoate Chemical compound CCOC(=O)C=C(C(C)=O)C(=O)C1CCCCC1 PIMSKFUWNYECEL-UHFFFAOYSA-N 0.000 claims description 3
- RBSPMIQCMGHSNU-UHFFFAOYSA-N ethyl 3-carbamoyl-4-oxopent-2-enoate Chemical compound CCOC(=O)C=C(C(C)=O)C(N)=O RBSPMIQCMGHSNU-UHFFFAOYSA-N 0.000 claims description 3
- IDYUUEKAPPIYBR-UHFFFAOYSA-N ethyl 4-oxo-3-(trimethylsilylmethylcarbamoyl)pent-2-enoate Chemical compound CCOC(=O)C=C(C(C)=O)C(=O)NC[Si](C)(C)C IDYUUEKAPPIYBR-UHFFFAOYSA-N 0.000 claims description 3
- VKTPASXYRPGXFL-UHFFFAOYSA-N methyl 2-carbamoyldec-2-enoate Chemical compound CCCCCCCC=C(C(N)=O)C(=O)OC VKTPASXYRPGXFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- PSHSMSYSLFPJEN-NTMALXAHSA-N 1-o-[2-(dimethylamino)ethyl] 4-o-ethyl (z)-2-acetylbut-2-enedioate Chemical compound CCOC(=O)\C=C(\C(C)=O)C(=O)OCCN(C)C PSHSMSYSLFPJEN-NTMALXAHSA-N 0.000 claims description 2
- GFDJYEMYBMLSJH-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)methylidene]-1-phenylbutane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)C)=CC1=CC=CC=C1O GFDJYEMYBMLSJH-UHFFFAOYSA-N 0.000 claims description 2
- DOMCVUKCALENDA-UHFFFAOYSA-N 3-octylidenepentane-2,4-dione Chemical compound CCCCCCCC=C(C(C)=O)C(C)=O DOMCVUKCALENDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- UDFKZBBVSIDXIL-UHFFFAOYSA-N diethyl 2-(3,7-dimethylocta-2,6-dienylidene)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC=C(C)CCC=C(C)C UDFKZBBVSIDXIL-UHFFFAOYSA-N 0.000 claims description 2
- DYLWMPQUPUHXOE-UHFFFAOYSA-N diethyl 2-(pyridin-2-ylmethylidene)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=CC=N1 DYLWMPQUPUHXOE-UHFFFAOYSA-N 0.000 claims description 2
- ATOPVVXJWMMBEG-UHFFFAOYSA-N diethyl 2-acetyl-3-methoxybutanedioate Chemical compound CCOC(=O)C(OC)C(C(C)=O)C(=O)OCC ATOPVVXJWMMBEG-UHFFFAOYSA-N 0.000 claims description 2
- SLLDNQSYNKTVFD-UHFFFAOYSA-N diethyl 2-butanoyl-3-ethoxybutanedioate Chemical compound CCCC(=O)C(C(=O)OCC)C(OCC)C(=O)OCC SLLDNQSYNKTVFD-UHFFFAOYSA-N 0.000 claims description 2
- KZROWENHXNDNOJ-UHFFFAOYSA-N diethyl 2-butanoyl-3-hydroxybutanedioate Chemical compound CCCC(=O)C(C(=O)OCC)C(O)C(=O)OCC KZROWENHXNDNOJ-UHFFFAOYSA-N 0.000 claims description 2
- OOCVMBSWVBDRPH-UHFFFAOYSA-N diethyl 2-decylidenepropanedioate Chemical compound CCCCCCCCCC=C(C(=O)OCC)C(=O)OCC OOCVMBSWVBDRPH-UHFFFAOYSA-N 0.000 claims description 2
- VFUIBCJBPVYRNW-UHFFFAOYSA-N diethyl 2-octylidenepropanedioate Chemical compound CCCCCCCC=C(C(=O)OCC)C(=O)OCC VFUIBCJBPVYRNW-UHFFFAOYSA-N 0.000 claims description 2
- ODHIUCXWGBUWRF-UHFFFAOYSA-N dimethyl 2-octylidenepropanedioate Chemical compound CCCCCCCC=C(C(=O)OC)C(=O)OC ODHIUCXWGBUWRF-UHFFFAOYSA-N 0.000 claims description 2
- GZFRHJPONRZEKP-UHFFFAOYSA-N ethyl 2-[(2-hydroxyphenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC=C1O GZFRHJPONRZEKP-UHFFFAOYSA-N 0.000 claims description 2
- QHRKNRZYJVTILX-UHFFFAOYSA-N ethyl 2-acetyldec-2-enoate Chemical compound CCCCCCCC=C(C(C)=O)C(=O)OCC QHRKNRZYJVTILX-UHFFFAOYSA-N 0.000 claims description 2
- QVLNMJLVSGGXOH-UHFFFAOYSA-N ethyl 2-acetylpent-2-enoate Chemical compound CCOC(=O)C(C(C)=O)=CCC QVLNMJLVSGGXOH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- PMHBYAGKMHEFPA-UHFFFAOYSA-N triethyl ethene-1,1,2-tricarboxylate Chemical compound CCOC(=O)C=C(C(=O)OCC)C(=O)OCC PMHBYAGKMHEFPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 39
- WRTHUMPHVMGUOC-UHFFFAOYSA-N 1-o-ethyl 4-o-(2-methoxyethyl) 3-acetyl-2-hydroxybutanedioate Chemical compound CCOC(=O)C(O)C(C(C)=O)C(=O)OCCOC WRTHUMPHVMGUOC-UHFFFAOYSA-N 0.000 claims 3
- OARZICFFWXUUQS-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-2-octylidenepropane-1,3-dione Chemical compound C=1C=C(C(C)(C)C)C=CC=1C(=O)C(=CCCCCCCC)C(=O)C1=CC=C(OC)C=C1 OARZICFFWXUUQS-UHFFFAOYSA-N 0.000 claims 2
- QNYTXFASIYXTPM-UHFFFAOYSA-N 1-o-benzyl 4-o-ethyl 2-acetylbut-2-enedioate Chemical compound CCOC(=O)C=C(C(C)=O)C(=O)OCC1=CC=CC=C1 QNYTXFASIYXTPM-UHFFFAOYSA-N 0.000 claims 2
- HOHCZDBRLMYZMU-UHFFFAOYSA-N diethyl 2-acetyl-3-hydroxybutanedioate Chemical compound CCOC(=O)C(O)C(C(C)=O)C(=O)OCC HOHCZDBRLMYZMU-UHFFFAOYSA-N 0.000 claims 2
- YQUQINJSZJWENV-UHFFFAOYSA-N ethyl 3-acetyl-2-hydroxy-4-oxopentanoate Chemical compound CCOC(=O)C(O)C(C(C)=O)C(C)=O YQUQINJSZJWENV-UHFFFAOYSA-N 0.000 claims 2
- ITLGHAXXSHESNE-UHFFFAOYSA-N 2-ethylidene-1-(1h-imidazol-5-yl)butane-1,3-dione Chemical compound CC=C(C(C)=O)C(=O)C1=CN=CN1 ITLGHAXXSHESNE-UHFFFAOYSA-N 0.000 claims 1
- VKPIBFFBMFUIPU-UHFFFAOYSA-N 2-propylidene-1-pyridin-4-ylbutane-1,3-dione Chemical compound CCC=C(C(C)=O)C(=O)C1=CC=NC=C1 VKPIBFFBMFUIPU-UHFFFAOYSA-N 0.000 claims 1
- NTFHVYNGNLOVQX-UHFFFAOYSA-N 3-[(2-hydroxy-5-nitrophenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC([N+]([O-])=O)=CC=C1O NTFHVYNGNLOVQX-UHFFFAOYSA-N 0.000 claims 1
- DDMYUHBSCSXTAY-UHFFFAOYSA-N 3-[(2-hydroxyphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=CC=C1O DDMYUHBSCSXTAY-UHFFFAOYSA-N 0.000 claims 1
- MJIRAKVJINGAOF-UHFFFAOYSA-N 3-[(3-ethoxy-4-hydroxyphenyl)methylidene]pentane-2,4-dione Chemical compound CCOC1=CC(C=C(C(C)=O)C(C)=O)=CC=C1O MJIRAKVJINGAOF-UHFFFAOYSA-N 0.000 claims 1
- JLFKCZFGOQIKLA-UHFFFAOYSA-N 3-[(5-acetyl-2-hydroxyphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC(C(C)=O)=CC=C1O JLFKCZFGOQIKLA-UHFFFAOYSA-N 0.000 claims 1
- STQAEANNWDXTAD-UHFFFAOYSA-N 4-acetyl-9-methyldeca-3,8-diene-2,5-dione Chemical compound CC(C)=CCCC(=O)C(C(C)=O)=CC(C)=O STQAEANNWDXTAD-UHFFFAOYSA-N 0.000 claims 1
- SCHBZNAIVCKWDG-UHFFFAOYSA-N 4-o-tert-butyl 1-o-ethyl 3-acetyl-2-hydroxybutanedioate Chemical compound CCOC(=O)C(O)C(C(C)=O)C(=O)OC(C)(C)C SCHBZNAIVCKWDG-UHFFFAOYSA-N 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- IFOLIMZSBBYWRW-UHFFFAOYSA-N benzyl 3-acetyl-4-oxopent-2-enoate Chemical compound CC(=O)C(C(C)=O)=CC(=O)OCC1=CC=CC=C1 IFOLIMZSBBYWRW-UHFFFAOYSA-N 0.000 claims 1
- JHJQXGCGLVPNQX-UHFFFAOYSA-N diethyl 2-(acetyloxymethylidene)propanedioate Chemical compound CCOC(=O)C(=COC(C)=O)C(=O)OCC JHJQXGCGLVPNQX-UHFFFAOYSA-N 0.000 claims 1
- HHWFOKLILKCKTC-UHFFFAOYSA-N diethyl 2-[(2-hydroxyphenyl)methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=CC=C1O HHWFOKLILKCKTC-UHFFFAOYSA-N 0.000 claims 1
- XUMZMKRVRIJEMR-UHFFFAOYSA-N diethyl 2-acetyl-3-[2-(2-ethoxyethoxy)ethoxy]butanedioate Chemical compound CCOCCOCCOC(C(=O)OCC)C(C(C)=O)C(=O)OCC XUMZMKRVRIJEMR-UHFFFAOYSA-N 0.000 claims 1
- KHCXKIQQZNPBDX-UHFFFAOYSA-N ethyl 2-hydroxy-3-(1h-imidazole-5-carbonyl)-4-oxopentanoate Chemical compound CCOC(=O)C(O)C(C(C)=O)C(=O)C1=CNC=N1 KHCXKIQQZNPBDX-UHFFFAOYSA-N 0.000 claims 1
- YQRAXLLUKHQLNQ-UHFFFAOYSA-N ethyl 3-acetyl-2-ethoxy-4-oxopentanoate Chemical compound CCOC(C(C(C)=O)C(C)=O)C(=O)OCC YQRAXLLUKHQLNQ-UHFFFAOYSA-N 0.000 claims 1
- RGNHIESYGXQDQU-UHFFFAOYSA-N ethyl 3-benzoyl-2-ethoxy-4-oxopentanoate Chemical compound CCOC(=O)C(OCC)C(C(C)=O)C(=O)C1=CC=CC=C1 RGNHIESYGXQDQU-UHFFFAOYSA-N 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 description 29
- 235000019645 odor Nutrition 0.000 description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 11
- NZQMQVJXSRMTCJ-UHFFFAOYSA-N 3-Methyl-hexanoic acid Chemical compound CCCC(C)CC(O)=O NZQMQVJXSRMTCJ-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 125000001624 naphthyl group Chemical group 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 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 8
- 230000009965 odorless effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- QMCVOSQFZZCSLN-VAWYXSNFSA-N dihexyl (e)-but-2-enedioate Chemical compound CCCCCCOC(=O)\C=C\C(=O)OCCCCCC QMCVOSQFZZCSLN-VAWYXSNFSA-N 0.000 description 6
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 210000004243 sweat Anatomy 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012496 blank sample Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- PHRRYVOQWOVNLF-UHFFFAOYSA-N 3-sulfanylbutan-1-ol Chemical compound CC(S)CCO PHRRYVOQWOVNLF-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000010411 cooking Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000001877 deodorizing effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0501237.2A GB0501237D0 (en) | 2005-01-21 | 2005-01-21 | Organic compounds |
| PCT/CH2006/000010 WO2006076821A1 (en) | 2005-01-21 | 2006-01-06 | 2 -c-substituted propane-1, 3 -dicarbonyl compounds and their use in neutralising malodour |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008528451A true JP2008528451A (ja) | 2008-07-31 |
| JP2008528451A5 JP2008528451A5 (enExample) | 2009-02-19 |
Family
ID=34259438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007551527A Pending JP2008528451A (ja) | 2005-01-21 | 2006-01-06 | 2−c置換プロパン−1,3−ジカルボニル化合物および悪臭中和におけるその使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20080305066A1 (enExample) |
| EP (1) | EP1838278A1 (enExample) |
| JP (1) | JP2008528451A (enExample) |
| KR (1) | KR20070097073A (enExample) |
| CN (1) | CN101106968A (enExample) |
| BR (1) | BRPI0614023A2 (enExample) |
| GB (1) | GB0501237D0 (enExample) |
| MX (1) | MX2007008551A (enExample) |
| WO (1) | WO2006076821A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0611770D0 (en) * | 2006-06-15 | 2006-07-26 | Givaudan Sa | Compounds |
| EP2272491A1 (fr) * | 2009-06-18 | 2011-01-12 | Robertet S.A. | Nouvelles compositions désodorisantes et produits désodorisants les renfermant |
| US8414870B2 (en) | 2010-12-06 | 2013-04-09 | Sytheon, Ltd. | Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers |
| US8617528B2 (en) | 2010-12-06 | 2013-12-31 | Sytheon Ltd. | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
| US9126890B2 (en) * | 2011-10-20 | 2015-09-08 | International Flavors & Fragrances Inc. | Low volatile reactive malodor counteractives and methods of use thereof |
| US20120294821A1 (en) * | 2011-05-20 | 2012-11-22 | International Flavors & Fragrances Inc. | Low Volatile Reactive Malodor Counteractives and Methods of Use Thereof |
| US10226544B2 (en) | 2015-06-05 | 2019-03-12 | International Flavors & Fragrances Inc. | Malodor counteracting compositions |
| US10549003B2 (en) | 2016-05-31 | 2020-02-04 | The Procter & Gamble Company | Method of demonstrating efficacy of a malodor counteractant product |
| CN111432851B (zh) * | 2017-11-22 | 2023-06-23 | 弗门尼舍有限公司 | 挥发性成分限制或消除对恶臭的感知的用途 |
| US12264295B2 (en) | 2019-03-20 | 2025-04-01 | Firmenich Sa | Encapsulated pro-perfume compounds |
| US20220259524A1 (en) | 2019-06-27 | 2022-08-18 | Firmenich Sa | Perfumed consumer products |
| EP4039244A1 (en) | 2021-02-04 | 2022-08-10 | Givaudan SA | Improvements in or relating to organic compounds |
| EP4504138A1 (en) * | 2022-06-21 | 2025-02-12 | Firmenich SA | Compositions for preventing, reducing, or ameliorating malodorous aldehydes and ketones, and uses thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4943917A (enExample) * | 1972-07-14 | 1974-04-25 | ||
| JPS6144843A (ja) * | 1984-06-23 | 1986-03-04 | ヘミツシエ・ヴエルケ・ヒユ−ルス・アクチエンゲゼルシヤフト | アルキリデン−及びアリ−リデン化合物の製法 |
| JPH04202122A (ja) * | 1990-11-28 | 1992-07-22 | Procter & Gamble Co:The | ジケトン脱臭組成物及び脱臭方法 |
| JPH1067628A (ja) * | 1996-06-24 | 1998-03-10 | Givaudan Roure Internatl Sa | ヒト悪臭抑制剤 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4810819A (en) * | 1984-04-06 | 1989-03-07 | Zambon Spa | Process for the preparation of optically active alpha-acrylalkanoic acids and novel intermediates thereof |
| DE3567209D1 (en) * | 1984-04-06 | 1989-02-09 | Zambon Spa | Optically active ketals, processes for their preparation and their use in the synthesis of apha-arylakanoic acids |
| US4830787A (en) * | 1987-08-13 | 1989-05-16 | Nabisco Brands, Inc. | Low calorie fat mimetics comprising carboxy/carboxylate esters |
| JP3647883B2 (ja) * | 1996-08-19 | 2005-05-18 | ザ、プロクター、エンド、ギャンブル、カンパニー | パーソナルケア用品のための芳香剤デリバリーシステム |
| GB0320441D0 (en) * | 2003-09-02 | 2003-10-01 | Givaudan Sa | Organic compounds |
-
2005
- 2005-01-21 GB GBGB0501237.2A patent/GB0501237D0/en not_active Ceased
-
2006
- 2006-01-06 CN CNA2006800028602A patent/CN101106968A/zh active Pending
- 2006-01-06 EP EP06700027A patent/EP1838278A1/en not_active Withdrawn
- 2006-01-06 BR BRPI0614023-8A patent/BRPI0614023A2/pt not_active IP Right Cessation
- 2006-01-06 KR KR1020077016600A patent/KR20070097073A/ko not_active Ceased
- 2006-01-06 US US11/814,057 patent/US20080305066A1/en not_active Abandoned
- 2006-01-06 MX MX2007008551A patent/MX2007008551A/es not_active Application Discontinuation
- 2006-01-06 JP JP2007551527A patent/JP2008528451A/ja active Pending
- 2006-01-06 WO PCT/CH2006/000010 patent/WO2006076821A1/en not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4943917A (enExample) * | 1972-07-14 | 1974-04-25 | ||
| JPS6144843A (ja) * | 1984-06-23 | 1986-03-04 | ヘミツシエ・ヴエルケ・ヒユ−ルス・アクチエンゲゼルシヤフト | アルキリデン−及びアリ−リデン化合物の製法 |
| JPH04202122A (ja) * | 1990-11-28 | 1992-07-22 | Procter & Gamble Co:The | ジケトン脱臭組成物及び脱臭方法 |
| JPH1067628A (ja) * | 1996-06-24 | 1998-03-10 | Givaudan Roure Internatl Sa | ヒト悪臭抑制剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0501237D0 (en) | 2005-03-02 |
| EP1838278A1 (en) | 2007-10-03 |
| KR20070097073A (ko) | 2007-10-02 |
| BRPI0614023A2 (pt) | 2011-03-01 |
| MX2007008551A (es) | 2007-08-14 |
| CN101106968A (zh) | 2008-01-16 |
| WO2006076821A1 (en) | 2006-07-27 |
| US20080305066A1 (en) | 2008-12-11 |
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