JP2010535718A5 - - Google Patents
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- Publication number
- JP2010535718A5 JP2010535718A5 JP2010519318A JP2010519318A JP2010535718A5 JP 2010535718 A5 JP2010535718 A5 JP 2010535718A5 JP 2010519318 A JP2010519318 A JP 2010519318A JP 2010519318 A JP2010519318 A JP 2010519318A JP 2010535718 A5 JP2010535718 A5 JP 2010535718A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- methyl
- alkyl
- formula
- alkenyl
- 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.)
- Granted
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 239000001257 hydrogen Substances 0.000 claims 75
- 150000002431 hydrogen Chemical class 0.000 claims 57
- 150000001875 compounds Chemical class 0.000 claims 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 26
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 22
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 125000004432 carbon atom Chemical group C* 0.000 claims 19
- 238000000034 method Methods 0.000 claims 14
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 11
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 11
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- -1 2-methyl-pent-2-en-5-yl Chemical group 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000003205 fragrance Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 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 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- 150000002009 diols Chemical class 0.000 claims 2
- 230000002708 enhancing effect Effects 0.000 claims 2
- 239000000796 flavoring agent Substances 0.000 claims 2
- 235000019634 flavors Nutrition 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 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 1
- VPNOCQFVZBZIMQ-UHFFFAOYSA-N (1-ethenyl-2,4-dimethylcyclohex-3-en-1-yl)methyl acetate Chemical compound CC1C=C(C)CCC1(COC(C)=O)C=C VPNOCQFVZBZIMQ-UHFFFAOYSA-N 0.000 claims 1
- MCRYLYSUOCEFGK-UHFFFAOYSA-N (4-ethenyl-2-methylcyclohexen-1-yl)methanol Chemical compound CC1=C(CO)CCC(C=C)C1 MCRYLYSUOCEFGK-UHFFFAOYSA-N 0.000 claims 1
- VSROEIKVPHHBSR-UHFFFAOYSA-N (4-ethenylcyclohexen-1-yl)methanol Chemical compound OCC1=CCC(C=C)CC1 VSROEIKVPHHBSR-UHFFFAOYSA-N 0.000 claims 1
- WCIIQJJGGQSZCM-UHFFFAOYSA-N 1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde Chemical compound C1=CCCC2CC(C=O)=CCC21 WCIIQJJGGQSZCM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 claims 1
- 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 claims 1
- LVXZHHVKUFRLBX-UHFFFAOYSA-N 1-(2,4-dimethyl-1-prop-1-en-2-ylcyclohex-3-en-1-yl)but-2-en-1-one Chemical compound CC=CC(=O)C1(C(C)=C)CCC(C)=CC1C LVXZHHVKUFRLBX-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 claims 1
- 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 claims 1
- 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 claims 1
- KVPDELIBSYIBGK-UHFFFAOYSA-N 1-(4-ethenylcyclohexen-1-yl)ethanol Chemical compound CC(O)C1=CCC(C=C)CC1 KVPDELIBSYIBGK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 claims 1
- 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 1
- XCMZINPUSVLPQO-UHFFFAOYSA-N 1-ethenyl-3,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1=C(C)CC(C=O)(C=C)CC1 XCMZINPUSVLPQO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- UWUUTYZVJJYXME-UHFFFAOYSA-N 1-ethenyl-4,5-dimethyl-2-(2-methylprop-1-enyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC1CC(C=C)(C=O)C(C=C(C)C)C=C1C UWUUTYZVJJYXME-UHFFFAOYSA-N 0.000 claims 1
- HCJAFBYGZGXACK-UHFFFAOYSA-N 1-ethenylcyclohex-3-ene-1-carbaldehyde Chemical compound C=CC1(C=O)CCC=CC1 HCJAFBYGZGXACK-UHFFFAOYSA-N 0.000 claims 1
- ZXOPLLGTQJCNDX-UHFFFAOYSA-N 1-methyl-3a,4,7,7a-tetrahydro-3h-indene-5-carbaldehyde Chemical compound C1C(C=O)=CCC2C(C)=CCC21 ZXOPLLGTQJCNDX-UHFFFAOYSA-N 0.000 claims 1
- RYFTZGITMYBDHI-UHFFFAOYSA-N 1-prop-1-en-2-ylcyclohex-3-ene-1-carbaldehyde Chemical compound CC(=C)C1(C=O)CCC=CC1 RYFTZGITMYBDHI-UHFFFAOYSA-N 0.000 claims 1
- GMVANJWNDFADSN-UHFFFAOYSA-N 2,4-dimethyl-1-(2-methylprop-1-enyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1(C=O)C=C(C)C GMVANJWNDFADSN-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 1
- NBUOSBPWABUQEX-UHFFFAOYSA-N 2-methyl-3a,4,7,7a-tetrahydro-3h-indene-5-carbaldehyde Chemical compound C1C=C(C=O)CC2CC(C)=CC21 NBUOSBPWABUQEX-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- IDHBUIGDSFWUEG-UHFFFAOYSA-N 3-propan-2-ylidene-3a,4,7,7a-tetrahydroindene-5-carbaldehyde Chemical compound C1C=C(C=O)CC2C(=C(C)C)C=CC21 IDHBUIGDSFWUEG-UHFFFAOYSA-N 0.000 claims 1
- SSJSDJGZGJAPQL-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-3h-inden-5-ylmethanol Chemical compound C1C(CO)=CCC2C=CCC21 SSJSDJGZGJAPQL-UHFFFAOYSA-N 0.000 claims 1
- XPPGFLPECUDBQG-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-3h-indene-5-carbaldehyde Chemical compound C1C(C=O)=CCC2C=CCC21 XPPGFLPECUDBQG-UHFFFAOYSA-N 0.000 claims 1
- YJYQQKJSOQDCNY-UHFFFAOYSA-N 4-ethenyl-2-methylcyclohexene-1-carbaldehyde Chemical compound CC1=C(C=O)CCC(C=C)C1 YJYQQKJSOQDCNY-UHFFFAOYSA-N 0.000 claims 1
- YQYKLWIDPWLECV-UHFFFAOYSA-N 4-ethenylcyclohexene-1-carbaldehyde Chemical compound C=CC1CCC(C=O)=CC1 YQYKLWIDPWLECV-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- YDFQDYQJUWVOHN-UHFFFAOYSA-N 6-methyl-3a,4,7,7a-tetrahydro-3h-indene-5-carbaldehyde Chemical compound C1C(C)=C(C=O)CC2CC=CC21 YDFQDYQJUWVOHN-UHFFFAOYSA-N 0.000 claims 1
- DSWTWKGGFPXYNO-UHFFFAOYSA-N 7-ethyl-3a,4,7,7a-tetrahydro-3h-indene-5-carbaldehyde Chemical compound CCC1C=C(C=O)CC2CC=CC12 DSWTWKGGFPXYNO-UHFFFAOYSA-N 0.000 claims 1
- RQXQBKXRGGBGEM-UHFFFAOYSA-N N-(3a,4,7,7a-tetrahydro-3H-inden-5-ylmethylidene)hydroxylamine Chemical compound C1C(C=NO)=CCC2C=CCC21 RQXQBKXRGGBGEM-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- OANSOJSBHVENEI-UHFFFAOYSA-N cyclohexene-1-carbaldehyde Chemical compound O=CC1=CCCCC1 OANSOJSBHVENEI-UHFFFAOYSA-N 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 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 1
- 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 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0715496.6 | 2007-08-10 | ||
| GBGB0715496.6A GB0715496D0 (en) | 2007-08-10 | 2007-08-10 | Novel process |
| PCT/CH2008/000337 WO2009021342A2 (en) | 2007-08-10 | 2008-08-07 | Cyclohexene derivatives and their use as odorants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010535718A JP2010535718A (ja) | 2010-11-25 |
| JP2010535718A5 true JP2010535718A5 (enExample) | 2013-03-14 |
| JP5563454B2 JP5563454B2 (ja) | 2014-07-30 |
Family
ID=38543274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010519318A Active JP5563454B2 (ja) | 2007-08-10 | 2008-08-07 | シクロヘキセン誘導体および着臭剤としてのそれらの使用 |
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 |
| WO2015148743A1 (en) * | 2014-03-26 | 2015-10-01 | The Procter & Gamble Company | Perfume systems |
| 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
-
2008
- 2008-08-07 MX MX2010001478A patent/MX2010001478A/es active IP Right Grant
- 2008-08-07 ES ES16181761T patent/ES2900863T3/es active Active
- 2008-08-07 CN CN200880102957XA patent/CN101796013B/zh active Active
- 2008-08-07 US US12/672,603 patent/US8304380B2/en not_active Expired - Fee Related
- 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 EP EP08772908A patent/EP2188242A2/en not_active Withdrawn
- 2008-08-07 BR BRPI0815373-6A patent/BRPI0815373B1/pt active IP Right Grant
-
2012
- 2012-10-08 US US13/647,161 patent/US8691746B2/en active Active
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