JPS5920649B2 - 新規香料化合物、その製造法および香料組成物 - Google Patents
新規香料化合物、その製造法および香料組成物Info
- Publication number
- JPS5920649B2 JPS5920649B2 JP52049803A JP4980377A JPS5920649B2 JP S5920649 B2 JPS5920649 B2 JP S5920649B2 JP 52049803 A JP52049803 A JP 52049803A JP 4980377 A JP4980377 A JP 4980377A JP S5920649 B2 JPS5920649 B2 JP S5920649B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- tables
- formulas
- methyl
- 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
- 239000000203 mixture Substances 0.000 title claims description 108
- 150000001875 compounds Chemical class 0.000 title claims description 80
- 239000003205 fragrance Substances 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 238000000034 method Methods 0.000 claims description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- 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 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 5
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 240000000513 Santalum album Species 0.000 description 33
- 235000008632 Santalum album Nutrition 0.000 description 33
- 229940126062 Compound A Drugs 0.000 description 28
- 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 28
- 239000010671 sandalwood oil Substances 0.000 description 28
- 230000000694 effects Effects 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- 239000000047 product Substances 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
- -1 trimethylcyclopent-3-ene-1-yl Chemical group 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 10
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000002304 perfume Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 235000019645 odor Nutrition 0.000 description 7
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 5
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- NQFUSWIGRKFAHK-BDNRQGISSA-N alpha-Pinene epoxide Natural products C([C@@H]1O[C@@]11C)[C@@H]2C(C)(C)[C@H]1C2 NQFUSWIGRKFAHK-BDNRQGISSA-N 0.000 description 5
- 229930006723 alpha-pinene oxide Natural products 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- SGIIQKAMTIJXBU-UHFFFAOYSA-N pentan-2-ol Chemical class CC[CH]C(C)O SGIIQKAMTIJXBU-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 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
- 238000006482 condensation reaction Methods 0.000 description 4
- 230000000881 depressing effect Effects 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- MDDYNMBUVLXLSB-UHFFFAOYSA-N hexan-3-ol Chemical compound C[CH+]CC(O)[CH+]C MDDYNMBUVLXLSB-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N n-hexan-3-ol Natural products CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 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 3
- 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 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 235000011613 Pinus brutia Nutrition 0.000 description 3
- 241000018646 Pinus brutia Species 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
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000002035 hexane extract Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- LABTWGUMFABVFG-UHFFFAOYSA-N 1-propenyl methyl ketone Natural products CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FEWIGMWODIRUJM-UHFFFAOYSA-N 4-hexen-3-one Chemical compound CCC(=O)C=CC FEWIGMWODIRUJM-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 244000283070 Abies balsamea Species 0.000 description 2
- 235000007173 Abies balsamea Nutrition 0.000 description 2
- 235000004710 Abies lasiocarpa Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000218645 Cedrus Species 0.000 description 2
- 239000002841 Lewis acid Substances 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000004808 allyl alcohols Chemical group 0.000 description 2
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 235000019568 aromas Nutrition 0.000 description 2
- 230000008901 benefit Effects 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
- 150000001721 carbon Chemical group 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 238000004821 distillation Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 229940035423 ethyl ether Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 230000007935 neutral effect Effects 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
- 230000000717 retained effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229940102001 zinc bromide Drugs 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- 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 description 1
- YRILEURMKYHART-UHFFFAOYSA-N 1,5,5-trimethyl-4-(3-methylpentyl)cyclopentene Chemical compound CCC(C)CCC1CC=C(C)C1(C)C YRILEURMKYHART-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- OGCGGWYLHSJRFY-VIFPVBQESA-N 2-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]acetaldehyde Chemical compound CC1=CC[C@@H](CC=O)C1(C)C OGCGGWYLHSJRFY-VIFPVBQESA-N 0.000 description 1
- 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 1
- 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 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FBXIZZSKBACHQV-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-one Chemical compound CC(=O)C(C)CCC1CC=C(C)C1(C)C FBXIZZSKBACHQV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 1
- 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 1
- HJCLNPPLOUYSBS-UHFFFAOYSA-N 6-(2,2,3-trimethylcyclopent-3-en-1-yl)hexan-3-one Chemical compound CCC(=O)CCCC1CC=C(C)C1(C)C HJCLNPPLOUYSBS-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 240000004731 Acer pseudoplatanus Species 0.000 description 1
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 244000068485 Convallaria majalis Species 0.000 description 1
- 235000009046 Convallaria majalis Nutrition 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- PDEQKAVEYSOLJX-UHFFFAOYSA-N Hexahydronerolidol Natural products C1C2C3(C)C2CC1C3(C)CCC=C(CO)C PDEQKAVEYSOLJX-UHFFFAOYSA-N 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910020828 NaAlH4 Inorganic materials 0.000 description 1
- 235000006485 Platanus occidentalis Nutrition 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- PDEQKAVEYSOLJX-AIEDFZFUSA-N alpha-Santalol Natural products CC(=CCC[C@@]1(C)[C@H]2C[C@@H]3[C@H](C2)[C@]13C)CO PDEQKAVEYSOLJX-AIEDFZFUSA-N 0.000 description 1
- 150000001386 alpha-pinene derivatives Chemical class 0.000 description 1
- PDEQKAVEYSOLJX-BKKZDLJQSA-N alpha-santalol Chemical compound C1C2[C@]3(C)C2C[C@H]1[C@@]3(C)CC/C=C(CO)/C PDEQKAVEYSOLJX-BKKZDLJQSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- OJYKYCDSGQGTRJ-INLOORNJSA-N beta-Santalol Natural products C1C[C@H]2C(=C)[C@](CC\C=C(CO)/C)(C)[C@@H]1C2 OJYKYCDSGQGTRJ-INLOORNJSA-N 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- OJYKYCDSGQGTRJ-GQYWAMEOSA-N beta-santalol Chemical compound C1C[C@H]2C(=C)[C@@](CC/C=C(CO)/C)(C)[C@@H]1C2 OJYKYCDSGQGTRJ-GQYWAMEOSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 101150084411 crn1 gene Proteins 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 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
- 230000003631 expected effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 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
- 230000009965 odorless effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UKIUSKWWNRYHOO-UHFFFAOYSA-N pent-1-yn-1-ol Chemical compound CCCC#CO UKIUSKWWNRYHOO-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
- 230000002085 persistent effect Effects 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
- 238000010791 quenching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000001711 saccadic effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 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 compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US000000681351 | 1976-04-29 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| JPS52133947A JPS52133947A (en) | 1977-11-09 |
| JPS5920649B2 true JPS5920649B2 (ja) | 1984-05-15 |
Family
ID=24734911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52049803A Expired JPS5920649B2 (ja) | 1976-04-29 | 1977-04-28 | 新規香料化合物、その製造法および香料組成物 |
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 |
| 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 |
| GB1563741A (en) | 1980-03-26 |
| AU506570B2 (en) | 1980-01-10 |
| ES458244A1 (es) | 1978-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5920649B2 (ja) | 新規香料化合物、その製造法および香料組成物 | |
| JP5479466B2 (ja) | 匂い物質として適するイソロンギホラニル誘導体 | |
| JP7177086B2 (ja) | 2,3,7-トリメチルオクタ-6-エニルアセテート及び3,7-ジメチル-2-メチレン-オクタ-6-エニルアセテート、並びにそれらの誘導体、並びに芳香化学物質としてのそれらの使用 | |
| CN101528655A (zh) | 用作增香剂的2,3,3-三甲基环戊-3-烯甲醛衍生物 | |
| GB1566092A (en) | Alkylcyclohexenones and their use as odorants and/or flavourants | |
| US4136066A (en) | 1-crotonyl-2,2,6-trimethylcyclohexane | |
| JP2022532827A (ja) | (3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-ヘキサメチルオクタヒドロ-4H-4a,9-メタノアズレノ[5,6-d][1,3]ジオキソール | |
| CA1136552A (en) | Acetyl trimethyl bicyclo non-ene as perfume | |
| JPS59176207A (ja) | 1−c2,6,6−トリメチルシクロヘキシル)−ヘキサン−3−オ−ル異性体混合物の製造法 | |
| JPS6312853B2 (enExample) | ||
| MX2009001378A (es) | Derivados de ciclopentano/ciclopenteno aldehido o cetona y su uso como odorizantes. | |
| DE69002571T2 (de) | Sauerstoffhaltige alizyklische Verbindungen, deren Anwendung als Riechstoffbestandteile und Verfahren zu deren Herstellung. | |
| US4278569A (en) | 2,2,3-Trimethyl-3-cyclopenten-1-ylalkyl, alkenyl and alkylidene, cyclohexanols, organo-leptic uses thereof in perfume compositions, colognes and perfumed articles | |
| US4130509A (en) | Perfume compositions containing cis- and trans-trimethylcyclohexylethyl ethers | |
| US5892104A (en) | Cycloheptenols and their derivatives, methods of making thereof, and utilization thereof as fragrances | |
| JP3850983B2 (ja) | 香料組成物または付香製品の匂い特性を付与、改善、増強または変性する方法、新規の二環式化合物、香料組成物、付香製品および新規の化合物の製造方法 | |
| DE69307188T2 (de) | Ungesättigte cyclische Alkohole, ihre Anwendung als Riechstoffbestandteile und deren Zwischenprodukte | |
| JPH04221335A (ja) | 新規環式ケトン、香料及び芳香製品の香り特性を付与し、改善し、高め又は変調する方法、香料組成物、及び、新規化合物を製造するための方法並びにそのための中間体 | |
| WO1980000839A1 (en) | Novel norcamphanyl-substituted pyrans,method for their synthesis and use thereof in perfumery | |
| JPS625123B2 (enExample) | ||
| US4517991A (en) | 3,4,5,6,6-Pentamethyl hexanol-2 and alkyl homologues thereof; process for preparing same and organoleptic uses thereof | |
| US3962339A (en) | Process for the production of bicyclo decenone derivatives | |
| JPS62185009A (ja) | 香料組成物 | |
| EP0023485A1 (en) | Substituted cyclic alcohols, methods of preparing and compositions containing same | |
| WO2003011803A1 (en) | Cyclopentanone derivative |