GB1563741A - Cyclopentene derivatives and their use as odourants - Google Patents
Cyclopentene derivatives and their use as odourants Download PDFInfo
- Publication number
- GB1563741A GB1563741A GB17807/77A GB1780777A GB1563741A GB 1563741 A GB1563741 A GB 1563741A GB 17807/77 A GB17807/77 A GB 17807/77A GB 1780777 A GB1780777 A GB 1780777A GB 1563741 A GB1563741 A GB 1563741A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- trimethylcyclopent
- pentan
- compound
- composition
- 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.)
- Expired
Links
- 239000003205 fragrance Substances 0.000 title claims description 28
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 35
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 claims description 23
- OGCGGWYLHSJRFY-SECBINFHSA-N (+)-alpha-Campholenal Natural products CC1=CC[C@H](CC=O)C1(C)C OGCGGWYLHSJRFY-SECBINFHSA-N 0.000 claims description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 20
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- -1 magnesium halide Chemical class 0.000 claims description 13
- QOACIWOGFMXQRO-UHFFFAOYSA-N 6-(2,2,3-trimethylcyclopent-3-en-1-yl)hexan-3-ol Chemical compound CCC(O)CCCC1CC=C(C)C1(C)C QOACIWOGFMXQRO-UHFFFAOYSA-N 0.000 claims description 10
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- TWUIRVFTSHQTGA-SOFGYWHQSA-N (e)-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-en-3-one Chemical compound CCC(=O)\C=C\CC1CC=C(C)C1(C)C TWUIRVFTSHQTGA-SOFGYWHQSA-N 0.000 claims description 4
- QQUWZMIGSXXJFV-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-3-en-2-one Chemical compound CC(=O)C(C)=CCC1CC=C(C)C1(C)C QQUWZMIGSXXJFV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- SYSAACBNNCUINP-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-3-en-2-ol Chemical compound CC(O)C(C)=CCC1CC=C(C)C1(C)C SYSAACBNNCUINP-UHFFFAOYSA-N 0.000 claims 2
- NGYMOTOXXHCHOC-KGPNIALWSA-N 3-methyl-5-[(1r)-2,2,3-trimethylcyclopent-3-en-1-yl]pentan-2-ol Chemical compound CC(O)C(C)CC[C@@H]1CC=C(C)C1(C)C NGYMOTOXXHCHOC-KGPNIALWSA-N 0.000 claims 1
- NGYMOTOXXHCHOC-GDKBPFBDSA-N 3-methyl-5-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]pentan-2-ol Chemical compound CC(O)C(C)CC[C@H]1CC=C(C)C1(C)C NGYMOTOXXHCHOC-GDKBPFBDSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000019645 odor Nutrition 0.000 description 78
- 240000000513 Santalum album Species 0.000 description 34
- 235000008632 Santalum album Nutrition 0.000 description 34
- 229940126062 Compound A Drugs 0.000 description 32
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 32
- 239000010671 sandalwood oil Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 150000001299 aldehydes Chemical class 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000002576 ketones Chemical class 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 239000012267 brine Substances 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 230000009102 absorption Effects 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 241000402754 Erythranthe moschata Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- NQFUSWIGRKFAHK-WHQQTDPMSA-N (1R,2S,4R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.02,4]octane Chemical compound C[C@@]12O[C@@H]1C[C@@H]1C[C@@H]2C1(C)C NQFUSWIGRKFAHK-WHQQTDPMSA-N 0.000 description 4
- DPSDTUAFBYJPJU-UHFFFAOYSA-N 3-ethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CCC(C(C)O)CCC1CC=C(C)C1(C)C DPSDTUAFBYJPJU-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000000834 fixative Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 150000003333 secondary alcohols Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- YSXRCIJQVHLMPJ-UHFFFAOYSA-N 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)butanal Chemical compound CCC(C=O)CCC1CC=C(C)C1(C)C YSXRCIJQVHLMPJ-UHFFFAOYSA-N 0.000 description 3
- AAPLYDDEQVREDC-UHFFFAOYSA-N 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal Chemical compound O=CC(C)=CCC1CC=C(C)C1(C)C AAPLYDDEQVREDC-UHFFFAOYSA-N 0.000 description 3
- QLWDKMHMOKIPHQ-UHFFFAOYSA-N 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)butanal Chemical compound O=CC(C)CCC1CC=C(C)C1(C)C QLWDKMHMOKIPHQ-UHFFFAOYSA-N 0.000 description 3
- HSFYRYDDBYGVJU-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopentyl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CCC(C)C1(C)C HSFYRYDDBYGVJU-UHFFFAOYSA-N 0.000 description 3
- NRVFUNVHEXIEHU-UHFFFAOYSA-N 5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-3-en-2-one Chemical compound CC(=O)C=CCC1CC=C(C)C1(C)C NRVFUNVHEXIEHU-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- 150000004808 allyl alcohols Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 3
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- KSEZPRJUTHMFGZ-UHFFFAOYSA-N 1-(3-ethyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(C(C)=O)C(CC)=C2 KSEZPRJUTHMFGZ-UHFFFAOYSA-N 0.000 description 2
- RJTHDCSHVMQKDQ-UHFFFAOYSA-N 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal Chemical compound CCC(C=O)=CCC1CC=C(C)C1(C)C RJTHDCSHVMQKDQ-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- YGBGMFUUSRYYOC-UHFFFAOYSA-N 4-methyl-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hexan-3-ol Chemical compound CCC(O)C(C)CCC1CC=C(C)C1(C)C YGBGMFUUSRYYOC-UHFFFAOYSA-N 0.000 description 2
- ZKKXUOROLFBYGR-UHFFFAOYSA-N 5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)CCCC1CC=C(C)C1(C)C ZKKXUOROLFBYGR-UHFFFAOYSA-N 0.000 description 2
- 235000007173 Abies balsamea Nutrition 0.000 description 2
- 244000283070 Abies balsamea Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 235000006484 Paeonia officinalis Nutrition 0.000 description 2
- 244000170916 Paeonia officinalis Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000002035 hexane extract Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
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- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 150000001728 carbonyl compounds Chemical class 0.000 description 1
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- WJSDHUCWMSHDCR-VMPITWQZSA-N cinnamyl acetate Natural products CC(=O)OC\C=C\C1=CC=CC=C1 WJSDHUCWMSHDCR-VMPITWQZSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
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- 239000002537 cosmetic Substances 0.000 description 1
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- 229940019836 cyclamen aldehyde Drugs 0.000 description 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical class C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
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- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-VENIDDJXSA-N palladium-100 Chemical compound [100Pd] KDLHZDBZIXYQEI-VENIDDJXSA-N 0.000 description 1
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
- GJYMQFMQRRNLCY-UHFFFAOYSA-N pent-3-en-2-ol Chemical compound CC=CC(C)O GJYMQFMQRRNLCY-UHFFFAOYSA-N 0.000 description 1
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 210000004357 third molar Anatomy 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- 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
- C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- C07C45/74—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 combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/21—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen 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
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (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 |
|---|---|---|---|
| US05/681,351 US4052341A (en) | 1976-04-29 | 1976-04-29 | 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol compound and perfume compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1563741A true GB1563741A (en) | 1980-03-26 |
Family
ID=24734911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17807/77A Expired GB1563741A (en) | 1976-04-29 | 1977-04-28 | Cyclopentene derivatives and their use as odourants |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4052341A (enExample) |
| JP (1) | JPS5920649B2 (enExample) |
| AU (1) | AU506570B2 (enExample) |
| BE (1) | BE854119A (enExample) |
| BR (1) | BR7702687A (enExample) |
| CA (1) | CA1084949A (enExample) |
| CH (3) | CH630589A5 (enExample) |
| DE (1) | DE2718549C3 (enExample) |
| ES (1) | ES458244A1 (enExample) |
| FR (1) | FR2349559A1 (enExample) |
| GB (1) | GB1563741A (enExample) |
| IT (1) | IT1125750B (enExample) |
| NL (1) | NL171572C (enExample) |
| SU (1) | SU722477A3 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4149020A (en) * | 1978-04-05 | 1979-04-10 | International Flavors & Fragrances Inc. | Intermediate for preparation of 2,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol |
| US4170577A (en) * | 1978-04-05 | 1979-10-09 | International Flavors & Fragrances Inc. | 2,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol perfume compositions |
| DE2827957C2 (de) * | 1978-06-26 | 1982-03-18 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Cyclopenten-Derivate, Verfahren zu deren Herstellung und ihre Verwendung als Riechstoffe |
| US4278569A (en) * | 1978-08-10 | 1981-07-14 | International Flavors & Fragrances Inc. | 2,2,3-Trimethyl-3-cyclopenten-1-ylalkyl, alkenyl and alkylidene, cyclohexanols, organo-leptic uses thereof in perfume compositions, colognes and perfumed articles |
| US4219451A (en) * | 1978-08-10 | 1980-08-26 | International Flavors & Fragrances Inc. | 2,2,3-Trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alcohols in perfume compositions |
| US4206091A (en) * | 1978-08-10 | 1980-06-03 | International Flavors & Fragrances Inc. | 2,2,3-Trimethyl-3-cyclopenten-1-yl-alkenyl and alkylidene cycloalkanones |
| US4173585A (en) * | 1978-08-10 | 1979-11-06 | International Flavors & Fragrances Inc. | 2,2,3-Trimethyl-3-cyclopenten-1-ylalkenyl- and alkylidene-cycloalkanones |
| JPS5536423A (en) * | 1978-09-08 | 1980-03-14 | Taiyo Koryo Kk | Perfume compound, its preparation, and perfumery composition |
| JPH0222052B2 (enExample) * | 1978-11-02 | 1990-05-17 | Furitsutsushe Dotsuji Ando Orukotsuto Inc | |
| WO1981000561A1 (fr) * | 1979-08-14 | 1981-03-05 | Firmenich & Cie | Alcools bicycliques et leur utilisation en tant qu'ingredients parfumants |
| US4289658A (en) * | 1979-09-19 | 1981-09-15 | Fritzsche Dodge & Olcott Inc. | 2-[-(2'2'3'-Trimethyl-3'-cyclopenten-1'-yl)-ethyliden]-and ethyl]-cyclopentanols |
| FR2496638A1 (fr) * | 1980-12-05 | 1982-06-25 | Roussel Uclaf | Nouveaux derives du cyclopentanol, leur procede de preparation et leur application comme agents parfumants |
| US4477683A (en) * | 1982-05-03 | 1984-10-16 | Givaudan Corporation | 3-Methyl-1-(2,3,4-and 2,4,4-trimethyl-1-cyclopentylidene) pent-2-en-4-one and isomers, and perfume compositions thereof |
| US4766002A (en) * | 1983-02-16 | 1988-08-23 | Givaudan Corporation | Flavoring with α-campholenic alcohol |
| DE3562901D1 (en) * | 1984-03-23 | 1988-06-30 | Firmenich & Cie | Hydroxylated derivatives of campholenic aldehyde, their use as flavouring agents and flavouring compositions containing them |
| DE3441902C1 (de) * | 1984-11-16 | 1986-01-30 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | 4-(2,2,3-Trimethylcyclopent-3-en-1-yl)-but-3-en-1-ole,Verfahren zu deren Herstellung und Verwendung als Riechstoffe |
| US4696766A (en) * | 1986-03-19 | 1987-09-29 | Givaudan Corporation | (2R*,3S*)-(E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol |
| US4619781A (en) * | 1985-09-20 | 1986-10-28 | International Flavors & Fragrances Inc. | Process for preparing mixture containing 2-campholenylidenbutanol, product produced thereby and perfumery uses thereof |
| US4666629A (en) * | 1985-09-20 | 1987-05-19 | International Flavors & Fragrances Inc. | Process for preparing mixture containing 2-campholenylidenbutanol, product produced thereby and perfumery uses thereof |
| DE3928242A1 (de) * | 1989-08-26 | 1991-02-28 | Basf Ag | Cycloalkylidenderivate |
| US5288701A (en) * | 1990-07-12 | 1994-02-22 | Givaudan-Roure Corporation | Derivatives of dihydrocampholenic aldehyde |
| DE19520103A1 (de) * | 1995-06-01 | 1996-12-05 | Henkel Kgaa | Verfahren zur Herstellung von Alkyl-substituierten Butenolen |
| EP0801049B1 (en) * | 1996-04-09 | 2001-11-21 | Givaudan SA | Cyclopentanebutanol derivatives as odorants |
| DE69729809T2 (de) * | 1996-04-09 | 2005-06-23 | Givaudan S.A. | Cyclopentanbutanolderivate |
| JP3400291B2 (ja) * | 1996-09-17 | 2003-04-28 | 高砂香料工業株式会社 | （ｅ）−（ｒ）−２−アルキル−４−（２，２，３−トリメチルシクロペント−３−エン−１−イル）−２−ブテン−１−オール誘導体、その製造方法および用途 |
| ES2186835T3 (es) * | 1996-11-06 | 2003-05-16 | Givaudan Sa | Isomeros opticos de derivados del aldehido canfolenico. |
| US6515186B2 (en) * | 2001-05-08 | 2003-02-04 | Millennium Specialty Chemicals | Process for obtaining alpha-campholenic aldehyde |
| GB0616002D0 (en) * | 2006-08-11 | 2006-09-20 | Givaudan Sa | Organic compounds |
| GB0620556D0 (en) * | 2006-10-18 | 2006-11-22 | Givauden Sa | Organic compounds |
| US7262329B1 (en) * | 2006-11-27 | 2007-08-28 | Millennium Specialty Chemicals, Inc. | Process for making intermediates for fragrance components from α-campholenic aldehyde |
| EP1930317A1 (en) * | 2006-12-08 | 2008-06-11 | V. Mane Fils | Use of campholenic derivatives as fragrant ingredients in perfumery and flavouring |
| ES2399942T3 (es) * | 2007-06-05 | 2013-04-04 | The Procter & Gamble Company | Sistemas de perfume |
| CN101125798B (zh) * | 2007-09-14 | 2010-05-26 | 杭州格林香料化学有限公司 | 一种3-龙脑烯基-2-丁醇的制备方法 |
| GB0802526D0 (en) * | 2008-02-12 | 2008-03-19 | Givaudan Sa | Organic compounds |
| US8481013B2 (en) * | 2008-11-26 | 2013-07-09 | Firmenich Sa | Compounds having sandalwood odors |
| CN101492347B (zh) * | 2009-01-06 | 2011-11-02 | 格林生物科技股份有限公司 | 用有机碱合成2-亚龙脑烯基丁醇的方法 |
| CN103449988B (zh) * | 2013-08-30 | 2015-11-18 | 广州百花香料股份有限公司 | 一种2-亚龙脑烯基丙醛的生产方法 |
| EP3042891B1 (en) * | 2013-09-06 | 2018-08-15 | Takasago International Corporation | Fragrance composition |
| CN103483151B (zh) * | 2013-10-10 | 2015-04-08 | 浦城县永芳香料科技有限公司 | 黑檀醇制备方法 |
| JP2018516257A (ja) * | 2015-05-29 | 2018-06-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | １，２，２−トリメチルシクロペンタン−１−イル部分を有する新規な香料 |
| ITUA20163604A1 (it) * | 2016-05-19 | 2017-11-19 | Giuliani Spa | Composti atti a promuovere la crescita dei capelli nell'uomo e/o a fermarne o ritardarne la caduta, e composizioni per tali usi |
| CN110590500A (zh) * | 2019-09-29 | 2019-12-20 | 格林生物科技股份有限公司 | 3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)戊-4-烯-2-醇的制备 |
| JP7498796B2 (ja) * | 2020-04-20 | 2024-06-12 | シムライズ アーゲー | オキサ・サンダルウッド型の芳香化合物 |
| US11999691B2 (en) | 2020-12-19 | 2024-06-04 | Actera Ingredients, Inc. | Odorless active agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68936C (de) * | J. BENK in Dresden-Altstadt | Selbsteinkassirender Kraftmesser | ||
| CH572009A5 (en) * | 1972-03-17 | 1976-01-30 | Givaudan & Cie Sa | 2-(3-hydroxy-pent(en)yl-3-iso-prop(en)yl-cyclopent-1-enes - prodn. by Grignard reaction and use as perfume (intermediates) |
| CH566113A5 (enExample) * | 1973-02-09 | 1975-09-15 | Firmenich & Cie |
-
1976
- 1976-04-29 US US05/681,351 patent/US4052341A/en not_active Expired - Lifetime
-
1977
- 1977-04-19 CH CH480477A patent/CH630589A5/de not_active IP Right Cessation
- 1977-04-25 FR FR7712379A patent/FR2349559A1/fr active Granted
- 1977-04-26 DE DE2718549A patent/DE2718549C3/de not_active Expired
- 1977-04-27 SU SU772475098A patent/SU722477A3/ru active
- 1977-04-28 GB GB17807/77A patent/GB1563741A/en not_active Expired
- 1977-04-28 ES ES458244A patent/ES458244A1/es not_active Expired
- 1977-04-28 CA CA277,222A patent/CA1084949A/en not_active Expired
- 1977-04-28 JP JP52049803A patent/JPS5920649B2/ja not_active Expired
- 1977-04-28 AU AU24666/77A patent/AU506570B2/en not_active Expired
- 1977-04-28 BR BR7702687A patent/BR7702687A/pt unknown
- 1977-04-29 IT IT23049/77A patent/IT1125750B/it active
- 1977-04-29 NL NLAANVRAGE7704737,A patent/NL171572C/xx not_active IP Right Cessation
- 1977-04-29 BE BE177144A patent/BE854119A/xx not_active IP Right Cessation
-
1981
- 1981-03-20 CH CH189981A patent/CH629462A5/de not_active IP Right Cessation
- 1981-03-20 CH CH189881A patent/CH629461A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2349559A1 (fr) | 1977-11-25 |
| DE2718549A1 (de) | 1977-11-10 |
| NL7704737A (nl) | 1977-11-01 |
| CH629462A5 (de) | 1982-04-30 |
| FR2349559B1 (enExample) | 1981-04-30 |
| JPS5920649B2 (ja) | 1984-05-15 |
| DE2718549C3 (de) | 1982-03-04 |
| US4052341A (en) | 1977-10-04 |
| CH630589A5 (de) | 1982-06-30 |
| DE2718549B2 (de) | 1981-03-12 |
| BR7702687A (pt) | 1978-03-21 |
| IT1125750B (it) | 1986-05-14 |
| CH629461A5 (de) | 1982-04-30 |
| SU722477A3 (ru) | 1980-03-15 |
| NL171572B (nl) | 1982-11-16 |
| CA1084949A (en) | 1980-09-02 |
| AU2466677A (en) | 1978-11-02 |
| JPS52133947A (en) | 1977-11-09 |
| NL171572C (nl) | 1983-04-18 |
| BE854119A (fr) | 1977-10-31 |
| AU506570B2 (en) | 1980-01-10 |
| ES458244A1 (es) | 1978-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19970427 |