JP2011514325A - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
- Publication number
- JP2011514325A JP2011514325A JP2010546194A JP2010546194A JP2011514325A JP 2011514325 A JP2011514325 A JP 2011514325A JP 2010546194 A JP2010546194 A JP 2010546194A JP 2010546194 A JP2010546194 A JP 2010546194A JP 2011514325 A JP2011514325 A JP 2011514325A
- Authority
- JP
- Japan
- Prior art keywords
- enyl
- trimethylcyclopent
- methyl
- bond
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000003205 fragrance Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
- 239000000796 flavoring agent Substances 0.000 claims abstract description 5
- 235000019634 flavors Nutrition 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 27
- -1 2,2,3-trimethyl-cyclopent-3-enyl Chemical group 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- HHZSLSRWAVPAFD-UHFFFAOYSA-N 2,2,3-trimethylcyclopentane-1-carbaldehyde Chemical compound CC1CCC(C=O)C1(C)C HHZSLSRWAVPAFD-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- OAOMPGIZMZXHLU-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)propan-1-ol Chemical compound CCC(O)C1CC=C(C)C1(C)C OAOMPGIZMZXHLU-UHFFFAOYSA-N 0.000 claims description 6
- CPKXZNAVHRUIPH-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)ethanol Chemical compound CC(O)C1CC=C(C)C1(C)C CPKXZNAVHRUIPH-UHFFFAOYSA-N 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- QNTPKYVXKBAWTC-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)prop-2-en-1-ol Chemical compound CC1=CCC(C(O)C=C)C1(C)C QNTPKYVXKBAWTC-UHFFFAOYSA-N 0.000 claims description 3
- FYTFEEDOWPNSJS-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)propan-1-one Chemical compound CCC(=O)C1CC=C(C)C1(C)C FYTFEEDOWPNSJS-UHFFFAOYSA-N 0.000 claims description 3
- KUSHNIVDXXIKCE-UHFFFAOYSA-N 2,2,3-trimethylcyclopent-3-ene-1-carbaldehyde Chemical compound CC1=CCC(C=O)C1(C)C KUSHNIVDXXIKCE-UHFFFAOYSA-N 0.000 claims description 3
- YQSAQFVWVQBMGL-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-2-ol Chemical compound CCC(C)(O)C1CC=C(C)C1(C)C YQSAQFVWVQBMGL-UHFFFAOYSA-N 0.000 claims description 3
- JMUBOBUZNRGCTJ-UHFFFAOYSA-N 2-methyl-1-(2,2,3-trimethylcyclopentyl)prop-2-en-1-ol Chemical compound CC1CCC(C(O)C(C)=C)C1(C)C JMUBOBUZNRGCTJ-UHFFFAOYSA-N 0.000 claims description 3
- BPHWXNLRLXYMGB-UHFFFAOYSA-N 3-methyl-1-(2,2,3-trimethylcyclopentyl)butan-1-ol Chemical compound CC(C)CC(O)C1CCC(C)C1(C)C BPHWXNLRLXYMGB-UHFFFAOYSA-N 0.000 claims description 3
- WPRDGOGWJNKEHH-UHFFFAOYSA-N 3-methyl-1-(2,2,3-trimethylcyclopentyl)butan-1-one Chemical compound CC(C)CC(=O)C1CCC(C)C1(C)C WPRDGOGWJNKEHH-UHFFFAOYSA-N 0.000 claims description 3
- ZZOAFVYNKNKPJG-UHFFFAOYSA-N 6-methyl-4-(2,2,3-trimethylcyclopentyl)hept-1-en-4-ol Chemical compound CC(C)CC(O)(CC=C)C1CCC(C)C1(C)C ZZOAFVYNKNKPJG-UHFFFAOYSA-N 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- HYMPODQLPOYLTG-WAYWQWQTSA-N (z)-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound C\C=C/C(O)C1CC=C(C)C1(C)C HYMPODQLPOYLTG-WAYWQWQTSA-N 0.000 claims description 2
- YXGUBJPWGFKWQA-UHFFFAOYSA-N 1-(2,2,3-trimethyl-1-cyclopent-3-enyl)ethanone Chemical compound CC(=O)C1CC=C(C)C1(C)C YXGUBJPWGFKWQA-UHFFFAOYSA-N 0.000 claims description 2
- KFCDMVJQHRKPNO-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-3-en-1-ol Chemical compound CC1=CCC(C(O)CC=C)C1(C)C KFCDMVJQHRKPNO-UHFFFAOYSA-N 0.000 claims description 2
- XYPXBNQYFAFAMV-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-3-en-1-one Chemical compound CC1=CCC(C(=O)CC=C)C1(C)C XYPXBNQYFAFAMV-UHFFFAOYSA-N 0.000 claims description 2
- ZRJGRSNZMWFFGP-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-5-en-1-ol Chemical compound CC1=CCC(C(O)CCCC=C)C1(C)C ZRJGRSNZMWFFGP-UHFFFAOYSA-N 0.000 claims description 2
- GAAOJCRIRRVZJE-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-1-one Chemical compound CC1=CCC(C(=O)CCC=C)C1(C)C GAAOJCRIRRVZJE-UHFFFAOYSA-N 0.000 claims description 2
- IZCZHTIXNPMNDH-UHFFFAOYSA-N 2,2-dimethyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-3-en-1-one Chemical compound CC1=CCC(C(=O)C(C)(C)C=C)C1(C)C IZCZHTIXNPMNDH-UHFFFAOYSA-N 0.000 claims description 2
- QTAJCFGIVAOUBH-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-5-en-2-ol Chemical compound CC1=CCC(C(C)(O)CCC=C)C1(C)C QTAJCFGIVAOUBH-UHFFFAOYSA-N 0.000 claims description 2
- MKBUMYZRPAQGFD-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)oct-7-en-2-ol Chemical compound CC1=CCC(C(C)(O)CCCCC=C)C1(C)C MKBUMYZRPAQGFD-UHFFFAOYSA-N 0.000 claims description 2
- QKIQXGNRJXNRRD-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CCCC(C)(O)C1CC=C(C)C1(C)C QKIQXGNRJXNRRD-UHFFFAOYSA-N 0.000 claims description 2
- VLFWYOZUFFSEFI-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)propan-2-ol Chemical compound CC1=CCC(C(C)(C)O)C1(C)C VLFWYOZUFFSEFI-UHFFFAOYSA-N 0.000 claims description 2
- LEUJPNKSWVIVGG-UHFFFAOYSA-N 2-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-1-one Chemical compound CCC(C)C(=O)C1CC=C(C)C1(C)C LEUJPNKSWVIVGG-UHFFFAOYSA-N 0.000 claims description 2
- PZMPFRFLCKLBMW-UHFFFAOYSA-N 2-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)prop-2-en-1-ol Chemical compound CC(=C)C(O)C1CC=C(C)C1(C)C PZMPFRFLCKLBMW-UHFFFAOYSA-N 0.000 claims description 2
- MOEUIAIYJBVIDC-UHFFFAOYSA-N 3-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-5-en-3-ol Chemical compound C=CCC(O)(CC)C1CC=C(C)C1(C)C MOEUIAIYJBVIDC-UHFFFAOYSA-N 0.000 claims description 2
- GCNAWFACHQGKCN-UHFFFAOYSA-N 3-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-1-ol Chemical compound CC(C)CC(O)C1CC=C(C)C1(C)C GCNAWFACHQGKCN-UHFFFAOYSA-N 0.000 claims description 2
- GAWPRSXIIADIJC-UHFFFAOYSA-N 4-(2,2,3-trimethylcyclopent-3-en-1-yl)oct-7-en-4-ol Chemical compound C=CCCC(O)(CCC)C1CC=C(C)C1(C)C GAWPRSXIIADIJC-UHFFFAOYSA-N 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- AQTUHJABKZECGA-UHFFFAOYSA-N hept-1-en-4-ol Chemical compound CCCC(O)CC=C AQTUHJABKZECGA-UHFFFAOYSA-N 0.000 claims 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 claims 1
- FSUXYWPILZJGCC-UHFFFAOYSA-N pent-4-en-1-ol Natural products CC=CCCO FSUXYWPILZJGCC-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 26
- 235000019645 odor Nutrition 0.000 description 16
- 150000001299 aldehydes Chemical class 0.000 description 15
- 240000002505 Pogostemon cablin Species 0.000 description 9
- 235000011751 Pogostemon cablin Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 8
- 230000000875 corresponding effect Effects 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229940022663 acetate Drugs 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 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 3
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000178870 Lavandula angustifolia Species 0.000 description 3
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000001102 lavandula vera Substances 0.000 description 3
- 235000018219 lavender Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 2
- RLHZQFIKXSZZJV-CHNYNBFLSA-N 1-[(3s)-1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl]ethanol Chemical compound CC1(C)[C@@H](C(O)C)CC2CC21C RLHZQFIKXSZZJV-CHNYNBFLSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 244000024873 Mentha crispa Species 0.000 description 2
- 235000014749 Mentha crispa Nutrition 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 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
- 238000007796 conventional method Methods 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000008241 heterogeneous mixture Substances 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 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
- 150000002678 macrocyclic compounds Chemical class 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/12—Alcohols containing rings other than six-membered aromatic rings containing five-membered rings
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/537—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0802526.4A GB0802526D0 (en) | 2008-02-12 | 2008-02-12 | Organic compounds |
| PCT/CH2009/000053 WO2009100554A1 (en) | 2008-02-12 | 2009-02-10 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011514325A true JP2011514325A (ja) | 2011-05-06 |
| JP2011514325A5 JP2011514325A5 (enExample) | 2013-04-11 |
Family
ID=39247479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010546194A Ceased JP2011514325A (ja) | 2008-02-12 | 2009-02-10 | 有機化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8445732B2 (enExample) |
| EP (1) | EP2252674B1 (enExample) |
| JP (1) | JP2011514325A (enExample) |
| CN (1) | CN101945985B (enExample) |
| AT (1) | ATE523580T1 (enExample) |
| BR (1) | BRPI0908367A2 (enExample) |
| ES (1) | ES2373271T3 (enExample) |
| GB (1) | GB0802526D0 (enExample) |
| MX (1) | MX2010008693A (enExample) |
| WO (1) | WO2009100554A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9370190B2 (en) | 2012-07-05 | 2016-06-21 | Eden Shield Ltd. | Pest repellents from plant extracts |
| GB201220341D0 (en) * | 2012-11-12 | 2012-12-26 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN104452430B (zh) * | 2014-10-23 | 2016-09-07 | 广东比伦生活用纸有限公司 | 一种超韧加香的生活用纸及其生产方法 |
| CN114437021B (zh) * | 2022-02-15 | 2023-05-09 | 东莞波顿香料有限公司 | 一种藿香香气化合物及其制备方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59159755A (ja) * | 1983-02-16 | 1984-09-10 | ジボーダン ― ルール （アンテルナショナル）ソシエテ アノニム | フレ−バ組成物 |
| EP0470426A2 (en) * | 1990-08-07 | 1992-02-12 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | 2,2,3-Trimethylcyclopentenyl acetone derivatives, organoleptic uses thereof and process for preparing same |
| JPH1036298A (ja) * | 1996-04-09 | 1998-02-10 | Givaudan Roure Internatl Sa | 新規着香剤 |
| JP2007507563A (ja) * | 2003-09-30 | 2007-03-29 | ジボダン エス エー | 有機化合物 |
| US20070298994A1 (en) * | 2004-06-30 | 2007-12-27 | Symrise Gmbh & Co. Kg | Use of 3-Mercapto-3-Methyl-Hexan-1-Ol for Use as Malodour Standard |
| JP2011511813A (ja) * | 2008-02-12 | 2011-04-14 | ジボダン エス エー | 有機化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4052341A (en) * | 1976-04-29 | 1977-10-04 | Givaudan Corporation | 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol compound and perfume compositions |
| EP0155591B1 (fr) | 1984-03-23 | 1988-05-25 | Firmenich Sa | Dérivés hydroxylés de l'aldéhyde campholénique, leur utilisation à titre d'ingrédients parfumants et composition parfumante les contenant |
| DD254382A1 (de) | 1986-12-09 | 1988-02-24 | Univ Leipzig | Verfahren zur herstellung von isomerem campholenaldehyd |
| US5288701A (en) | 1990-07-12 | 1994-02-22 | Givaudan-Roure Corporation | Derivatives of dihydrocampholenic aldehyde |
| EP1008579B1 (en) * | 1996-04-09 | 2004-07-07 | Givaudan SA | Cyclopentenebutanol derivatives |
| GB0616002D0 (en) | 2006-08-11 | 2006-09-20 | Givaudan Sa | Organic compounds |
| GB0620556D0 (en) | 2006-10-18 | 2006-11-22 | Givauden Sa | Organic compounds |
-
2008
- 2008-02-12 GB GBGB0802526.4A patent/GB0802526D0/en not_active Ceased
-
2009
- 2009-02-10 CN CN200980104960XA patent/CN101945985B/zh not_active Expired - Fee Related
- 2009-02-10 EP EP09711211A patent/EP2252674B1/en not_active Not-in-force
- 2009-02-10 BR BRPI0908367-7A patent/BRPI0908367A2/pt not_active IP Right Cessation
- 2009-02-10 ES ES09711211T patent/ES2373271T3/es active Active
- 2009-02-10 JP JP2010546194A patent/JP2011514325A/ja not_active Ceased
- 2009-02-10 MX MX2010008693A patent/MX2010008693A/es active IP Right Grant
- 2009-02-10 US US12/865,403 patent/US8445732B2/en not_active Expired - Fee Related
- 2009-02-10 AT AT09711211T patent/ATE523580T1/de not_active IP Right Cessation
- 2009-02-10 WO PCT/CH2009/000053 patent/WO2009100554A1/en not_active Ceased
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59159755A (ja) * | 1983-02-16 | 1984-09-10 | ジボーダン ― ルール （アンテルナショナル）ソシエテ アノニム | フレ−バ組成物 |
| EP0470426A2 (en) * | 1990-08-07 | 1992-02-12 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | 2,2,3-Trimethylcyclopentenyl acetone derivatives, organoleptic uses thereof and process for preparing same |
| JPH1036298A (ja) * | 1996-04-09 | 1998-02-10 | Givaudan Roure Internatl Sa | 新規着香剤 |
| JP2007507563A (ja) * | 2003-09-30 | 2007-03-29 | ジボダン エス エー | 有機化合物 |
| US20070298994A1 (en) * | 2004-06-30 | 2007-12-27 | Symrise Gmbh & Co. Kg | Use of 3-Mercapto-3-Methyl-Hexan-1-Ol for Use as Malodour Standard |
| JP2011511813A (ja) * | 2008-02-12 | 2011-04-14 | ジボダン エス エー | 有機化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009100554A1 (en) | 2009-08-20 |
| MX2010008693A (es) | 2010-08-30 |
| US20100331427A1 (en) | 2010-12-30 |
| ES2373271T3 (es) | 2012-02-01 |
| CN101945985A (zh) | 2011-01-12 |
| EP2252674B1 (en) | 2011-09-07 |
| US8445732B2 (en) | 2013-05-21 |
| GB0802526D0 (en) | 2008-03-19 |
| BRPI0908367A2 (pt) | 2015-07-28 |
| EP2252674A1 (en) | 2010-11-24 |
| CN101945985B (zh) | 2013-05-29 |
| ATE523580T1 (de) | 2011-09-15 |
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