ES2900863T3 - Derivados de ciclohexeno y su uso como odorante - Google Patents
Derivados de ciclohexeno y su uso como odorante Download PDFInfo
- Publication number
- ES2900863T3 ES2900863T3 ES16181761T ES16181761T ES2900863T3 ES 2900863 T3 ES2900863 T3 ES 2900863T3 ES 16181761 T ES16181761 T ES 16181761T ES 16181761 T ES16181761 T ES 16181761T ES 2900863 T3 ES2900863 T3 ES 2900863T3
- Authority
- ES
- Spain
- Prior art keywords
- hydrogen
- methyl
- alkyl
- alkenyl
- formula
- 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.)
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- 239000003205 fragrance Substances 0.000 title claims description 29
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 103
- 239000001257 hydrogen Substances 0.000 claims abstract description 102
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 29
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 150000001993 dienes Chemical class 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000011065 in-situ storage Methods 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 69
- -1 carboxylic acid halide Chemical class 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 13
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000001299 aldehydes Chemical class 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 7
- HCJAFBYGZGXACK-UHFFFAOYSA-N 1-ethenylcyclohex-3-ene-1-carbaldehyde Chemical compound C=CC1(C=O)CCC=CC1 HCJAFBYGZGXACK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- LTSTZDGSNJVQKU-UHFFFAOYSA-N 1-ethenyl-3-methylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1=CCCC(C=O)(C=C)C1 LTSTZDGSNJVQKU-UHFFFAOYSA-N 0.000 claims description 6
- QLHHGSKVTLQUKC-UHFFFAOYSA-N (1-ethenyl-2,4-dimethylcyclohex-3-en-1-yl)methanol Chemical compound CC1C=C(C)CCC1(CO)C=C QLHHGSKVTLQUKC-UHFFFAOYSA-N 0.000 claims description 5
- JJUIXSDDQNOAKL-UHFFFAOYSA-N 1-(1-ethenyl-2,4-dimethylcyclohex-3-en-1-yl)but-3-en-1-ol Chemical compound CC1C=C(C)CCC1(C=C)C(O)CC=C JJUIXSDDQNOAKL-UHFFFAOYSA-N 0.000 claims description 5
- CUUQGRRTJCGPEG-UHFFFAOYSA-N 1-(1-ethenyl-2,4-dimethylcyclohex-3-en-1-yl)ethanol Chemical compound CC(O)C1(C=C)CCC(C)=CC1C CUUQGRRTJCGPEG-UHFFFAOYSA-N 0.000 claims description 5
- MZVUQLFYBIIVGJ-UHFFFAOYSA-N 1-(1-ethenyl-2,4-dimethylcyclohex-3-en-1-yl)but-3-en-1-one Chemical compound CC1C=C(C)CCC1(C=C)C(=O)CC=C MZVUQLFYBIIVGJ-UHFFFAOYSA-N 0.000 claims description 4
- UTFFKDUFBDMQIQ-UHFFFAOYSA-N 1-(1-ethenyl-2,4-dimethylcyclohex-3-en-1-yl)ethanone Chemical compound CC1C=C(C)CCC1(C=C)C(C)=O UTFFKDUFBDMQIQ-UHFFFAOYSA-N 0.000 claims description 4
- HDXXCVSLLOOHCF-UHFFFAOYSA-N n-[(1-ethenyl-3-methylcyclohex-3-en-1-yl)methylidene]hydroxylamine Chemical compound CC1=CCCC(C=NO)(C=C)C1 HDXXCVSLLOOHCF-UHFFFAOYSA-N 0.000 claims description 4
- MLJRXERKGLELMB-UHFFFAOYSA-N n-[(1-ethenyl-4-methylcyclohex-3-en-1-yl)methylidene]hydroxylamine Chemical compound CC1=CCC(C=NO)(C=C)CC1 MLJRXERKGLELMB-UHFFFAOYSA-N 0.000 claims description 4
- ULDKKODFYNVPMS-UHFFFAOYSA-N 1-(cyclopenten-1-yl)-2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound C1(=CCCC1)C1(C(C=C(CC1)C)C)C=O ULDKKODFYNVPMS-UHFFFAOYSA-N 0.000 claims description 3
- BLEKWGULEIACGA-UHFFFAOYSA-N 1-but-1-enyl-2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CCC=CC1(C=O)CCC(C)=CC1C BLEKWGULEIACGA-UHFFFAOYSA-N 0.000 claims description 3
- WLWBKMODJZUPHC-UHFFFAOYSA-N 1-buta-1,3-dienyl-2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1(C=O)C=CC=C WLWBKMODJZUPHC-UHFFFAOYSA-N 0.000 claims description 3
- PTRRFJIJMLKTET-UHFFFAOYSA-N 1-ethenyl-2-methyl-4-(4-methylpent-3-enyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(CCC=C(C)C)CCC1(C=C)C=O PTRRFJIJMLKTET-UHFFFAOYSA-N 0.000 claims description 3
- KVPRTQWFMOYROG-UHFFFAOYSA-N 2-methyl-1-(2-methylprop-1-enyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=CCCC1(C=O)C=C(C)C KVPRTQWFMOYROG-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- ZIWXFYOINQODEF-UHFFFAOYSA-N 1-[2,4-dimethyl-1-(2-methylprop-1-enyl)cyclohex-3-en-1-yl]ethanol Chemical compound CC(C)=CC1(C(O)C)CCC(C)=CC1C ZIWXFYOINQODEF-UHFFFAOYSA-N 0.000 claims description 2
- WMJWVVTZKVBZIN-UHFFFAOYSA-N COC(C1(CC=C(CC1)C)C=C)OC Chemical compound COC(C1(CC=C(CC1)C)C=C)OC WMJWVVTZKVBZIN-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
- 239000000203 mixture Substances 0.000 description 50
- 238000005160 1H NMR spectroscopy Methods 0.000 description 44
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 44
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 26
- 239000000047 product Substances 0.000 description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 11
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- YQYKLWIDPWLECV-UHFFFAOYSA-N 4-ethenylcyclohexene-1-carbaldehyde Chemical compound C=CC1CCC(C=O)=CC1 YQYKLWIDPWLECV-UHFFFAOYSA-N 0.000 description 8
- 235000011430 Malus pumila Nutrition 0.000 description 8
- 235000015103 Malus silvestris Nutrition 0.000 description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 8
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 8
- 239000000796 flavoring agent Substances 0.000 description 8
- 235000019634 flavors Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
- RCJMVGJKROQDCB-SNAWJCMRSA-N (3e)-2-methylpenta-1,3-diene Chemical compound C\C=C\C(C)=C RCJMVGJKROQDCB-SNAWJCMRSA-N 0.000 description 6
- RCJMVGJKROQDCB-UHFFFAOYSA-N 1,3-dimethyl-1,3-butadiene Natural products CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RUMOYJJNUMEFDD-UHFFFAOYSA-N perillyl aldehyde Chemical compound CC(=C)C1CCC(C=O)=CC1 RUMOYJJNUMEFDD-UHFFFAOYSA-N 0.000 description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
- RUMOYJJNUMEFDD-SNVBAGLBSA-N (R)-(+)-Perillaldehyde Natural products CC(=C)[C@H]1CCC(C=O)=CC1 RUMOYJJNUMEFDD-SNVBAGLBSA-N 0.000 description 5
- ARXWAZQEZBTNIM-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1(C=C)C=O ARXWAZQEZBTNIM-UHFFFAOYSA-N 0.000 description 5
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- NPBIJNXYQJVUNF-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)ethanol Chemical compound CC(O)C1(C(C)=C)CCC(C)=CC1C NPBIJNXYQJVUNF-UHFFFAOYSA-N 0.000 description 4
- NDUZIMWWLPFMTD-UHFFFAOYSA-N 2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1(C=O)C(C)=C NDUZIMWWLPFMTD-UHFFFAOYSA-N 0.000 description 4
- MBDOYVRWFFCFHM-UHFFFAOYSA-N 2-hexenal Chemical compound CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 4
- 244000241257 Cucumis melo Species 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NDTYTMIUWGWIMO-UHFFFAOYSA-N perillyl alcohol Chemical compound CC(=C)C1CCC(CO)=CC1 NDTYTMIUWGWIMO-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- OQJYBQXYFOQAES-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)but-3-en-1-ol Chemical compound CC1C=C(C)CCC1(C(O)CC=C)C(C)=C OQJYBQXYFOQAES-UHFFFAOYSA-N 0.000 description 3
- XEMDJTWRJXQQRA-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)but-3-en-1-one Chemical compound CC1C=C(C)CCC1(C(C)=C)C(=O)CC=C XEMDJTWRJXQQRA-UHFFFAOYSA-N 0.000 description 3
- HPNYRWXBUHDLFO-UHFFFAOYSA-N 1-(3a,4,7,7a-tetrahydro-3h-inden-5-yl)ethanone Chemical compound C1C(C(=O)C)=CCC2C=CCC21 HPNYRWXBUHDLFO-UHFFFAOYSA-N 0.000 description 3
- IMUMRIXLOYBAMK-UHFFFAOYSA-N 1-ethenyl-4-methylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1=CCC(C=O)(C=C)CC1 IMUMRIXLOYBAMK-UHFFFAOYSA-N 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 3
- OZAUVUBFUFWDRD-UHFFFAOYSA-N 3-methyl-1-prop-1-en-2-ylcyclohex-3-ene-1-carbaldehyde Chemical compound CC(=C)C1(C=O)CCC=C(C)C1 OZAUVUBFUFWDRD-UHFFFAOYSA-N 0.000 description 3
- JZLKKMAUZMMUMS-UHFFFAOYSA-N 4-(6-methylhepta-1,5-dien-2-yl)cyclohexene-1-carbaldehyde Chemical compound CC(C)=CCCC(=C)C1CCC(C=O)=CC1 JZLKKMAUZMMUMS-UHFFFAOYSA-N 0.000 description 3
- YJYQQKJSOQDCNY-UHFFFAOYSA-N 4-ethenyl-2-methylcyclohexene-1-carbaldehyde Chemical compound CC1=C(C=O)CCC(C=C)C1 YJYQQKJSOQDCNY-UHFFFAOYSA-N 0.000 description 3
- TYVGPQBBYDIUFO-UHFFFAOYSA-N 4-methyl-1-prop-1-en-2-ylcyclohex-3-ene-1-carbaldehyde Chemical compound CC(=C)C1(C=O)CCC(C)=CC1 TYVGPQBBYDIUFO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 240000000560 Citrus x paradisi Species 0.000 description 3
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 2
- MCRYLYSUOCEFGK-UHFFFAOYSA-N (4-ethenyl-2-methylcyclohexen-1-yl)methanol Chemical compound CC1=C(CO)CCC(C=C)C1 MCRYLYSUOCEFGK-UHFFFAOYSA-N 0.000 description 2
- VSROEIKVPHHBSR-UHFFFAOYSA-N (4-ethenylcyclohexen-1-yl)methanol Chemical compound OCC1=CCC(C=C)CC1 VSROEIKVPHHBSR-UHFFFAOYSA-N 0.000 description 2
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 2
- PQTQALPIDVGBOL-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)-2-methylpropan-1-ol Chemical compound CC(C)C(O)C1(C(C)=C)CCC(C)=CC1C PQTQALPIDVGBOL-UHFFFAOYSA-N 0.000 description 2
- KEQFMNVNGVFWID-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)-2-methylpropan-1-one Chemical compound CC(C)C(=O)C1(C(C)=C)CCC(C)=CC1C KEQFMNVNGVFWID-UHFFFAOYSA-N 0.000 description 2
- ATRBOFYZSKBXFV-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)ethanone Chemical compound CC1C=C(C)CCC1(C(C)=C)C(C)=O ATRBOFYZSKBXFV-UHFFFAOYSA-N 0.000 description 2
- XDSUUYDJCAZDMC-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)ethyl acetate Chemical compound CC(=O)OC(C)C1(C(C)=C)CCC(C)=CC1C XDSUUYDJCAZDMC-UHFFFAOYSA-N 0.000 description 2
- KVPDELIBSYIBGK-UHFFFAOYSA-N 1-(4-ethenylcyclohexen-1-yl)ethanol Chemical compound CC(O)C1=CCC(C=C)CC1 KVPDELIBSYIBGK-UHFFFAOYSA-N 0.000 description 2
- MBDOYVRWFFCFHM-SNAWJCMRSA-N 2-Hexenal Natural products CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- XPPGFLPECUDBQG-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-3h-indene-5-carbaldehyde Chemical compound C1C(C=O)=CCC2C=CCC21 XPPGFLPECUDBQG-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2026—Hydroxy compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
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- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
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- C07C47/44—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
- C07C47/445—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic containing a condensed ring system
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- C07C47/00—Compounds having —CHO groups
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- C07C47/45—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings having unsaturation outside the rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- 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
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- C11B9/00—Essential oils; Perfumes
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- C11B9/00—Essential oils; Perfumes
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- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
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- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
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- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0057—Spiro compounds
-
- 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
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six 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
- C11B9/0069—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
-
- 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
- C11B9/0088—Spiro compounds
-
- 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
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0715496.6A GB0715496D0 (en) | 2007-08-10 | 2007-08-10 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2900863T3 true ES2900863T3 (es) | 2022-03-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16181761T Active ES2900863T3 (es) | 2007-08-10 | 2008-08-07 | Derivados de ciclohexeno y su uso como odorante |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8304380B2 (enExample) |
| EP (2) | EP3112338B1 (enExample) |
| JP (1) | JP5563454B2 (enExample) |
| CN (1) | CN101796013B (enExample) |
| BR (1) | BRPI0815373B1 (enExample) |
| ES (1) | ES2900863T3 (enExample) |
| GB (1) | GB0715496D0 (enExample) |
| MX (1) | MX2010001478A (enExample) |
| WO (1) | WO2009021342A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0715496D0 (en) * | 2007-08-10 | 2007-09-19 | Givauden Sa | Novel process |
| GB201013474D0 (en) * | 2010-08-11 | 2010-09-22 | Givaudan Sa | Organic compounds |
| DE102011005947A1 (de) * | 2011-03-23 | 2012-09-27 | Henkel Ag & Co. Kgaa | Diels-Alder-Addukte als thermisch spaltbare Riechstoffvorläufer |
| GB201201287D0 (en) | 2012-01-26 | 2012-03-07 | Givaudan Sa | Compositions |
| JP2017511402A (ja) * | 2014-03-26 | 2017-04-20 | ザ プロクター アンド ギャンブル カンパニー | 香料系 |
| CN104433927B (zh) * | 2014-10-23 | 2017-11-10 | 广东比伦生活用纸有限公司 | 一种手帕纸的加香工艺及制得的香味手帕纸 |
| GB201613013D0 (en) * | 2016-07-27 | 2016-09-07 | Givaudan Sa | Organic compound |
| CN109651149B (zh) * | 2017-10-11 | 2021-06-01 | 中国科学院大连化学物理研究所 | 一种制备1,2-环己烷二甲酸酯或邻苯二甲酸酯的方法 |
| CN111495289B (zh) * | 2020-04-27 | 2021-01-12 | 肇庆市高要华新香料有限公司 | 一种气液两相连续反应装置及山梨醛的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3067244A (en) * | 1958-03-06 | 1962-12-04 | Shell Oil Co | Process for the production of dielsalder adducts |
| US3641156A (en) * | 1968-04-29 | 1972-02-08 | Hoffmann La Roche | Juvabione and derivatives thereof |
| NL7304990A (enExample) | 1972-05-01 | 1973-11-05 | ||
| US4010207A (en) | 1976-01-15 | 1977-03-01 | International Flavors & Fragrances Inc. | Process for the alkylation of α, β-unsaturated aldehydes |
| GB1591342A (en) | 1976-08-11 | 1981-06-17 | Int Flavors & Fragrances Inc | Carbonyl compounds processes for preparing same and uses of such carbonyl compounds in affecting the aroma and taste of foodstuffs robaccos beverages perfumes and perfumed articles |
| JPH0657120B2 (ja) * | 1986-11-18 | 1994-08-03 | 長谷川香料株式会社 | 持続性紫蘇フレーバー剤 |
| DE19961030A1 (de) * | 1999-12-16 | 2001-06-21 | Haarmann & Reimer Gmbh | Aromen und Aromakompositionen enthaltend 4,8-Dimethyl-3,7-nonadien-2-on und ein Verfahren zu dessen Herstellung |
| JP2002179509A (ja) * | 2000-12-12 | 2002-06-26 | Takasago Internatl Corp | 抗カビ香料組成物 |
| US20050191257A1 (en) | 2004-02-27 | 2005-09-01 | John Brahms | Dry deodorant containing a sesquiterpene alcohol and zinc oxide |
| GB0715496D0 (en) * | 2007-08-10 | 2007-09-19 | Givauden Sa | Novel process |
-
2007
- 2007-08-10 GB GBGB0715496.6A patent/GB0715496D0/en not_active Ceased
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2008
- 2008-08-07 WO PCT/CH2008/000337 patent/WO2009021342A2/en not_active Ceased
- 2008-08-07 JP JP2010519318A patent/JP5563454B2/ja active Active
- 2008-08-07 EP EP16181761.4A patent/EP3112338B1/en active Active
- 2008-08-07 CN CN200880102957XA patent/CN101796013B/zh active Active
- 2008-08-07 ES ES16181761T patent/ES2900863T3/es active Active
- 2008-08-07 MX MX2010001478A patent/MX2010001478A/es active IP Right Grant
- 2008-08-07 US US12/672,603 patent/US8304380B2/en not_active Expired - Fee Related
- 2008-08-07 EP EP08772908A patent/EP2188242A2/en not_active Withdrawn
- 2008-08-07 BR BRPI0815373-6A patent/BRPI0815373B1/pt active IP Right Grant
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2012
- 2012-10-08 US US13/647,161 patent/US8691746B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010535718A (ja) | 2010-11-25 |
| BRPI0815373B1 (pt) | 2018-01-02 |
| EP3112338A2 (en) | 2017-01-04 |
| US20100204084A1 (en) | 2010-08-12 |
| EP2188242A2 (en) | 2010-05-26 |
| EP3112338B1 (en) | 2021-09-29 |
| CN101796013B (zh) | 2013-09-04 |
| GB0715496D0 (en) | 2007-09-19 |
| EP3112338A3 (en) | 2017-03-22 |
| CN101796013A (zh) | 2010-08-04 |
| MX2010001478A (es) | 2010-03-01 |
| US8691746B2 (en) | 2014-04-08 |
| WO2009021342A3 (en) | 2009-07-30 |
| US20130035278A1 (en) | 2013-02-07 |
| WO2009021342A2 (en) | 2009-02-19 |
| US8304380B2 (en) | 2012-11-06 |
| BRPI0815373A2 (pt) | 2015-02-10 |
| JP5563454B2 (ja) | 2014-07-30 |
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