JP2016530227A - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
- Publication number
- JP2016530227A JP2016530227A JP2016522536A JP2016522536A JP2016530227A JP 2016530227 A JP2016530227 A JP 2016530227A JP 2016522536 A JP2016522536 A JP 2016522536A JP 2016522536 A JP2016522536 A JP 2016522536A JP 2016530227 A JP2016530227 A JP 2016530227A
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- methyl
- phenyl
- nmr
- butanal
- 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
- 150000002894 organic compounds Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000003205 fragrance Substances 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 29
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- -1 propen-2-yl Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- BMCWFGPRVVKAAC-UHFFFAOYSA-N CC(C)CCCc1cccc(c1)C(C)CC=O Chemical compound CC(C)CCCc1cccc(c1)C(C)CC=O BMCWFGPRVVKAAC-UHFFFAOYSA-N 0.000 claims description 7
- VEABUJASOCQMFM-UHFFFAOYSA-N CC(C)CCc1cccc(c1)C(C)CC=O Chemical compound CC(C)CCc1cccc(c1)C(C)CC=O VEABUJASOCQMFM-UHFFFAOYSA-N 0.000 claims description 7
- OPHSGYDJCHDYAG-UHFFFAOYSA-N CC(Cc1cccc(CCC(C)=C)c1)C=O Chemical compound CC(Cc1cccc(CCC(C)=C)c1)C=O OPHSGYDJCHDYAG-UHFFFAOYSA-N 0.000 claims description 7
- PXKYIPVGPBVGRO-UHFFFAOYSA-N CC(C)CCc1cccc(CC(C)C=O)c1 Chemical compound CC(C)CCc1cccc(CC(C)C=O)c1 PXKYIPVGPBVGRO-UHFFFAOYSA-N 0.000 claims description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 5
- ZCDRBAQCSBNJOR-UHFFFAOYSA-N CC(C=O)C(C)c1cccc(CCC(C)=C)c1 Chemical compound CC(C=O)C(C)c1cccc(CCC(C)=C)c1 ZCDRBAQCSBNJOR-UHFFFAOYSA-N 0.000 claims description 4
- YRKWOYHYNUHUSL-UHFFFAOYSA-N CC(Cc1cccc(CCC2CC2)c1)C=O Chemical compound CC(Cc1cccc(CCC2CC2)c1)C=O YRKWOYHYNUHUSL-UHFFFAOYSA-N 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 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 claims 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical class O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 45
- 239000000243 solution Substances 0.000 description 32
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 31
- 235000019645 odor Nutrition 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- 238000003756 stirring Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000002537 cosmetic Substances 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 238000000023 Kugelrohr distillation Methods 0.000 description 7
- 239000012300 argon atmosphere Substances 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002198 insoluble material Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 4
- JLXQSHYFGIBTPI-UHFFFAOYSA-N CC(C)(O)CCc1cccc(C=O)c1 Chemical compound CC(C)(O)CCc1cccc(C=O)c1 JLXQSHYFGIBTPI-UHFFFAOYSA-N 0.000 description 4
- 244000068485 Convallaria majalis Species 0.000 description 4
- 235000009046 Convallaria majalis Nutrition 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006383 Hayashi-Miyaura coupling reaction Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 2
- FOHUDAFFAVYJHU-FMIVXFBMSA-N (E)-3-[3-(3-hydroxy-3-methylbutyl)phenyl]-2-methylprop-2-enal Chemical compound OC(CCC=1C=C(C=CC=1)/C=C(/C=O)\C)(C)C FOHUDAFFAVYJHU-FMIVXFBMSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OPNDWUNGMWNXNB-UHFFFAOYSA-N 1,5-benzodioxepin-3-one Chemical class O1CC(=O)COC2=CC=CC=C21 OPNDWUNGMWNXNB-UHFFFAOYSA-N 0.000 description 2
- VERUENJPKLDCKE-UHFFFAOYSA-N 1-(3-bromophenyl)-4-methylpentan-1-ol Chemical compound CC(C)CCC(O)C1=CC=CC(Br)=C1 VERUENJPKLDCKE-UHFFFAOYSA-N 0.000 description 2
- NNUWHKZHDXKRMU-UHFFFAOYSA-N 1-chloro-3-(3-methylbut-3-enyl)benzene Chemical compound CC(=C)CCC1=CC=CC(Cl)=C1 NNUWHKZHDXKRMU-UHFFFAOYSA-N 0.000 description 2
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 2
- UDKPLWDQSJVECZ-QPJJXVBHSA-N 3-[3-[(E)-4-methylpent-1-enyl]phenyl]butanal Chemical compound CC(C/C=C/C=1C=C(C=CC=1)C(CC=O)C)C UDKPLWDQSJVECZ-QPJJXVBHSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-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
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XBQWMWGFGMXVAH-UHFFFAOYSA-N CC(=C)CCc1cccc(c1)B(O)O Chemical compound CC(=C)CCc1cccc(c1)B(O)O XBQWMWGFGMXVAH-UHFFFAOYSA-N 0.000 description 2
- BMCWFGPRVVKAAC-AWEZNQCLSA-N CC(C)CCCc1cccc(c1)[C@@H](C)CC=O Chemical compound CC(C)CCCc1cccc(c1)[C@@H](C)CC=O BMCWFGPRVVKAAC-AWEZNQCLSA-N 0.000 description 2
- BMCWFGPRVVKAAC-CQSZACIVSA-N CC(C)CCCc1cccc(c1)[C@H](C)CC=O Chemical compound CC(C)CCCc1cccc(c1)[C@H](C)CC=O BMCWFGPRVVKAAC-CQSZACIVSA-N 0.000 description 2
- VWYBQRRMQKYRLL-FPLPWBNLSA-N CC(C)\C=C/c1cccc(C(C)CC=O)c1 Chemical compound CC(C)\C=C/c1cccc(C(C)CC=O)c1 VWYBQRRMQKYRLL-FPLPWBNLSA-N 0.000 description 2
- CHTBJZBIJSJUSQ-UHFFFAOYSA-N CC(CC=O)c1cccc(CCC2CC2)c1 Chemical compound CC(CC=O)c1cccc(CCC2CC2)c1 CHTBJZBIJSJUSQ-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 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
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-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
- 238000004587 chromatography analysis Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 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
- 150000002170 ethers Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002678 macrocyclic compounds Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 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
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000000746 purification Methods 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
- 230000035807 sensation Effects 0.000 description 2
- 235000019615 sensations Nutrition 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 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
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 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
- 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
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- DCSCXTJOXBUFGB-MQWKRIRWSA-N (5r)-2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one Chemical compound CC1=CC(=O)[C@H]2C(C)(C)C1C2 DCSCXTJOXBUFGB-MQWKRIRWSA-N 0.000 description 1
- NEJDKFPXHQRVMV-UHFFFAOYSA-N (E)-2-Methyl-2-buten-1-ol Natural products CC=C(C)CO NEJDKFPXHQRVMV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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Abstract
Description
R1およびR2は、独立して、水素およびメチルから選択され、ただし少なくともR1またはR2のいずれかは、メチルであり;
R3は、プロパ−2−イル、プロペン−2−イルおよびシクロプロピルから選択され;ならびに
nは、1または2である。
本発明者らは、顕著な匂いの特徴に加えて、式(I)で表され、式中R2がメチルである化合物が、対応する安息香酸誘導体への酵素媒介分解を受けず、したがって特に好ましいことを見出した。
3−(3−(2−シクロプロピルエチル)フェニル)−2−メチルプロパナールが引用され得、それは顕著な匂いの特徴を有するのみならず、極めて低い匂いしきい値をも有し、それによって、効果を達成するための極めて少量でのその使用が可能になる。
− エッセンシャルオイルおよびエキス、例えば海狸香、コスツス根油、オークモスアブソリュート、ゼラニウム油、ツリーモスアブソリュート、メボウキ油、果実油、例えばベルガモット油およびマンダリン油、ギンバイカ油、パルマローザ油、パチョリ油、プチグレン油、ジャスミン油、バラ油、ビャクダン油、ヨモギ油、ラベンダー油またはイランイランノキ油;
− エステルおよびラクトン、例えば酢酸ベンジル、酢酸セドリル、γ−デカラクトン、Helvetolide(登録商標)、γ−ウンデカラクトンまたは酢酸ベチベニル;
− 大員環、例えばAmbrettolide、エチレンブラシレートまたはExaltolide (登録商標);ならびに
・複素環、例えばイソブチルキノリン。
本発明はまた、以下のもの:
a)匂い物質としての少なくとも1種の式(I)で表される化合物;および
b)消費者製品ベース
を含む、フレグランスが付与された物品を提供する。
(a)化粧用スキンケア製品、特に浴用化粧品、皮膚洗浄およびクレンジング製品、スキンケア製品、アイメイク、リップケア製品、ネイルケア製品、肌に直接触れるケア製品、フットケア製品;
(b)特定の効果を有する化粧品製品、特に日焼け止め剤, 日焼けの製品, 脱色(de-pigmenting)製品, 体臭防止剤, 制汗剤, 脱毛剤およびひげそり製品;
(c)化粧用デンタルケア製品、特にデンタルケアおよび口腔ケア製品、歯のケア製品、義歯用クリーナー、義歯用接着剤;ならびに
(d)化粧用ヘアケア製品、特にヘアシャンプー、ヘアケア製品、頭髪セット製品、頭髪成形製品および頭髪着色製品。
R1およびR2は、独立して、水素およびメチルから選択され、ただし少なくともR1またはR2のいずれかは、メチルであり;
R3は、プロパ−2−イル、プロペン−2−イルおよびシクロプロピルから選択され;ならびに
nは、1または2である。
マグネシウム粉末(turning)(5.91、243mmol)を、20mLの無水エーテルに、250mLの3つ首フラスコ中で加えた。アルゴン雰囲気下で、最初に、1−ブロモ−3−メチルブタン(36.7g、243mmol)をエーテル(100mL)に溶解した溶液5mLを、40℃に時々加熱しながら加えて、反応を開始する。反応を開始した後、混合物を氷水浴中で5℃に放冷し、残りを激しく撹拌しながら30分以内に滴加した。完全な添加の後、反応物を30分間還流させた。
匂いの説明:アルデヒド様、水様−海洋様、金属の様相。
匂いの説明:水様−海洋様、花様−アルデヒド様、わずかに金属様およびグリーンレモンを連想させる。
匂いの説明:花様−アルデヒド様、脂肪様−バター様、甘い−メロン方向にフルーティー、(S)−異性体より海洋様でなく、強力でない。
(S)−3−(3−(4−メチルペンチル)フェニル)ブタナール(0.70g、31%の収率、87%ee)。
匂いの説明:水様−海洋様、花様−アルデヒド様、脂肪様−バター様、わずかに金属様、グリーン柑橘類。
アルゴン雰囲気下で、3−クロロ−2−メチルプロパ−1−エン(10.0g、0.110mol)を、マグネシウム粉末(48.3g、2.00mol)を無水THF(600mL)に懸濁させた撹拌した懸濁液に加えた。反応が開始した後、さらなる3−クロロ−2−メチルプロパ−1−エン(170g、1.88mol)を、30〜50℃の温度を保持するような速度で撹拌し、氷浴中で時々冷却しながら滴加した。完全な添加の後、反応混合物を60℃でさらに30分間撹拌し、次に25℃に放冷する。1−クロロ−3−(クロロメチル)ベンゼン(213g、1.32mol)を、氷水浴中で冷却しながら1時間以内に滴加して、30℃より低い温度を保持した。
匂いの説明:花様−アルデヒド様、水様−海洋様、わずかに金属様。
匂いの説明:花様−アルデヒド様、水様−海洋様、わずかに脂肪様−金属様。
アルゴン雰囲気下で、750mLの反応フラスコ中で、トリフェニルホスフィン(2.00g、7.63mmol)、Pd(OAc)2(500mg、2.23mmol)およびヨウ化銅(I)(400mg、2.1mmol)を、脱気したトルエン(300mL)に溶解した。激しく撹拌しながら、3−ブロモベンズアルデヒド(55.5g、300mmol)を加え、続いて15分間の撹拌の後に、トリエチルアミン(45.0g、445mmol)を加えた。反応混合物を45℃に加熱し、それによって発熱反応が始まり、温度は60分以内に75℃に上昇し、(Et)3NHBrの沈殿を伴った。発熱反応が終わり、温度が再び降下を開始した際、反応混合物を90℃に10分間加熱し、2−メチルブタ−3−イン−2−オール(25.2g、300mmol)を2時間の期間にわたって滴加し、反応温度を90〜95℃に保持した。撹拌しながら90〜95℃にさらに2.75時間加熱した後に、反応混合物を室温に放冷し、MTBE(300mL)および水(300ml)を、10分の期間の間用心深く加えた。
匂いの説明:花様−アルデヒド様、水様−海洋様、わずかに金属様。
−30℃で、カリウムtert−ブトキシド(7.73g、68.8mmol)をTHF(25mL)に溶解した溶液を、イソブチルトリフェニルホスホニウムブロミド(25.0g、62.6mmol)をTHF(100mL)に溶解した溶液に加えた。この温度で2時間撹拌した後、3−ブロモベンズアルデヒドを−25℃で加え、冷却浴を取り外し、反応混合物を室温に放置して加温した。室温で3時間撹拌した後、反応混合物を、氷水(1:1)上に注いだ。有機層を分離し、水性のものをエーテルで抽出した。合わせた有機抽出物を、水およびブラインで洗浄し、次にMgSO4で乾燥した。溶媒をロータリーエバボレーター上で除去して、39.9gの粗生成物をオレンジ色−茶色がかった液体として得、それをフラッシュクロマトグラフィー(ペンタン)によってさらに精製して、11.1g(78%)の(Z)−1−ブロモ−3−(3−メチルブタ−1−エニル)ベンゼンを提供した。
匂いの説明:花様、海洋様−水様、アルデヒド様。
匂いの説明:水様−海洋様、花様、アルデヒド様、それと共にいくらかのオゾン様特徴。
−22℃で、カリウムtert−ブトキシド(1.38g、12.3mmol)をTHF(12mL)に溶解した溶液を、シクロプロピルトリフェニルホスホニウムブロミド(4.90g、12.3mmol)をTHF(24mL)に溶解した撹拌した溶液に加え、それに際して反応温度は−15℃に上昇し、色はオレンジ色に変化した。−25℃〜−15℃で1時間撹拌した後、反応混合物を−25℃に冷却し、3−ブロモベンズアルデヒド(2.28g、12.33mmol)をTHF(12mL)に溶解した溶液を加え、それに際して反応温度は−4℃に上昇し、色はベージュ色に変化した。冷却浴を取り外し、反応混合物を室温で30分間撹拌し、その後氷水(1:1)上に注いだ。生成物をエーテルで2回抽出し、合わせた有機抽出物を水で洗浄し、硫酸ナトリウムで乾燥した。溶媒をロータリーエバボレーター上で除去して、5.79gの粗生成物を得、それをフラッシュクロマトグラフィー(エーテル:ペンタン、1:100)によって精製して、1.75g(61%)の(Z)−1−ブロモ−3−(2−シクロプロピルビニル)ベンゼンを帯黄色油として提供した。
匂いの説明:海洋様、水様、花様、グリーン−アルデヒド様、クリーミー、卵白をわずかに連想させる
匂いの説明:花様−アルデヒド様、水様−海洋様、わずかに金属様。
3−(3−(2−シクロプロピルビニル)フェニル)ブタナール(2.70g、12.6mmol)を酢酸エチル(50ml)に溶解した溶液を、触媒量のPd/C(10%)の存在下で水素雰囲気下で15時間撹拌した。溶液をシリカゲルのパッドで濾過し、真空中で濃縮した。残留物をシリカゲル上のクロマトグラフィーによって精製して、3−(3−(2−シクロプロピルエチル)フェニル)ブタナール(0.4g、13%)を無色油として得た。
匂いの説明:アルデヒド様水様花様、海洋様、わずかにバター様、クリーミー。
Pd(OAc)2(158mg、0.33mmol)およびトリフェニルホスフィン(173mg、0.66mmol)のDMPU(20ml)中の混合物を、室温で10分間撹拌した。1−ブロモ−3−(3−メチルブタ−3−エン−1−イル)ベンゼン(7.43g、33mmol)を、暗いが透明な溶液に加えた。混合物をさらに3分間撹拌し、2−メチルブタ−2−エン−1−オール(5.69g、66mmol)およびNaHCO3(3.33g、39.6mmol)を加えた。混合物を130℃に加熱し、この温度で15時間放置して撹拌した。反応混合物を冷却し、氷水(200ml)中に注いだ。混合物を、セライトのパッドで濾過し、エーテルで3回抽出した。合わせた有機相を、水およびブラインで洗浄し、Na2SO4で乾燥し、真空中で濃縮した。残留物をシリカゲル上のクロマトグラフィーによって精製し、145℃/0.13mbarで蒸留して、2−メチル−3−(3−(3−メチルブタ−3−エン−1−イル)フェニル)ブタナール(0.75g、9%)を6:4の比率での2種の異性体の混合物として得た(無色油)。
匂いの説明:花様−アルデヒド様、水様−海洋様、わずかに金属様、ジヒドロファルネサール(dihydro farnesal)様。
Claims (8)
- 式(I)
R1およびR2は、独立して、水素およびメチルから選択され、ただし少なくともR1またはR2のいずれかは、メチルであり;
R3は、プロパ−2−イル、プロペン−2−イルおよびシクロプロピルから選択され;ならびに
nは、1または2である、
で表される化合物。 - 3−(3−(4−メチルペンチル)フェニル)ブタナール、3−(3−イソペンチルフェニル)−2−メチルプロパナール、2−メチル−3−(3−(3−メチルブタ−3−エン−1−イル)フェニル)−プロパナール、3−(3−イソペンチルフェニル)ブタナール、3−(3−(2−シクロプロピルエチル)フェニル)−2−メチルプロパナール、3−(3−(2−シクロプロピルエチル)フェニル)ブタナール、および2−メチル−3−(3−(3−メチルブタ−3−エン−1−イル)フェニル)ブタナールから選択される、請求項1に記載の化合物。
- R2がメチルである、請求項1に記載の化合物。
- (S)鏡像異性体において富化されている、請求項1に記載の化合物。
- 式(I)
R1およびR2は、独立して、水素およびメチルから選択され、ただし少なくともR1またはR2のいずれかは、メチルであり;
R3は、プロパ−2−イル、プロペン−2−イルおよびシクロプロピルから選択され;ならびに
nは、1または2である、
で表される化合物の、フレグランスとしての使用。 - 消費者製品ベースを改善、増強または改変する方法であって、それに、式(I)
R1およびR2は、独立して、水素およびメチルから選択され、ただし少なくともR1またはR2のいずれかは、メチルであり;
R3は、プロパ−2−イル、プロペン−2−イルおよびシクロプロピルから選択され;ならびに
nは、1または2である、
で表される化合物またはその混合物を加えることによる、前記方法。 - a.少なくとも1種の式(I)
R1およびR2は、独立して、水素およびメチルから選択され、ただし少なくともR1またはR2のいずれかは、メチルであり;
R3は、プロパ−2−イル、プロペン−2−イルおよびシクロプロピルから選択され;ならびに
nは、1または2である、
で表される化合物;ならびに
b.少なくとも1種の既知の匂い物質
を含む、フレグランス組成物。 - a.少なくとも1種の式(I)
R1およびR2は、独立して、水素およびメチルから選択され、ただし少なくともR1またはR2のいずれかは、メチルであり;
R3は、プロパ−2−イル、プロペン−2−イルおよびシクロプロピルから選択され;ならびに
nは、1または2である、
で表される化合物;ならびに
b.消費者製品ベース
を含む、フレグランスが付与された物品。
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Cited By (2)
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WO2021075517A1 (ja) * | 2019-10-17 | 2021-04-22 | 三菱瓦斯化学株式会社 | アルデヒド化合物及びその製造方法、並びに香料組成物 |
WO2023243499A1 (ja) * | 2022-06-17 | 2023-12-21 | 三菱瓦斯化学株式会社 | アルデヒド組成物 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2017009175A1 (en) * | 2015-07-14 | 2017-01-19 | Firmenich Sa | Compound having a muguet odor |
WO2018134221A1 (en) | 2017-01-18 | 2018-07-26 | Firmenich Sa | Composition having a muguet odor |
WO2018134220A1 (en) | 2017-01-18 | 2018-07-26 | Firmenich Sa | Composition having a muguet odor |
EP4314216A1 (en) * | 2021-04-01 | 2024-02-07 | Basf Se | 2-(2-(3-methylbut-2-en-1yl)phenyl) propanal and mixtures thereof as aroma ingredient |
CN114133982B (zh) * | 2021-11-23 | 2024-02-27 | 万华化学集团股份有限公司 | 一种制备具有玫瑰香味的香料的方法及组合物原料 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2079751A (en) * | 1980-07-09 | 1982-01-27 | Albright & Wilson | Process for the production of alkyl-phenyl propanals and some products thereof |
WO2010091969A1 (en) * | 2009-02-13 | 2010-08-19 | Basf Se | Lily of the valley-type fragrance compositions |
JP2013508331A (ja) * | 2009-10-23 | 2013-03-07 | ビーエーエスエフ ソシエタス・ヨーロピア | 異性化によるm−置換フェニルアルカノールの製造方法 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3548006A (en) | 1963-03-15 | 1970-12-15 | Rhone Poulenc Sa | Aldehydes useful in perfumery |
FR1364620A (fr) | 1963-03-15 | 1964-06-26 | Rhone Poulenc Sa | Aldéhyde p. isobutyldihydrocinnamique |
BE672280A (ja) * | 1964-11-13 | 1966-05-12 | ||
JPH03221599A (ja) | 1990-01-26 | 1991-09-30 | Takasago Internatl Corp | 香料組成物 |
US5095152A (en) | 1990-11-21 | 1992-03-10 | Union Camp Corporation | Novel heptamethyl indane compound |
WO1994027946A1 (fr) | 1993-05-26 | 1994-12-08 | Firmenich S.A. | Composes aromatiques nouveaux et leur utilisation en parfumerie |
DE69516036T2 (de) | 1994-05-31 | 2000-12-21 | Firmenich & Cie | Aromatische Verbindungen und ihre Verwendung in der Parfümerie |
US6465410B1 (en) | 1999-04-30 | 2002-10-15 | The Procter & Gamble | Laundry detergent and/or fabric care composition comprising a modified antimicrobial protein |
US6342612B1 (en) | 2001-01-26 | 2002-01-29 | International Flavors & Fragrances Inc. | Indane aldehydes and derivatives |
US8188126B2 (en) | 2002-05-16 | 2012-05-29 | Pierre Fabre Medicament | Imidazolic compounds and use thereof as alpha-2 adrenergic receptors |
EP2013209B1 (en) | 2006-04-26 | 2011-01-19 | Actelion Pharmaceuticals Ltd. | Pyrazolo-tetrahydropyridine derivatives as orexin receptor antagonists |
US7652053B2 (en) | 2006-11-30 | 2010-01-26 | Hoffmann-La Roche Inc. | Diaminocycloalkane MCH receptor antagonists |
US8754028B2 (en) | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
DE102009001569A1 (de) | 2009-03-16 | 2010-09-23 | Henkel Ag & Co. Kgaa | Lilial-Substitut |
TW201238603A (en) * | 2011-03-10 | 2012-10-01 | Lonza Ag | Method for preparation of 3-(2,3-dimethylphenyl)-2-butenal |
JP5893146B2 (ja) | 2011-09-30 | 2016-03-23 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | Lilial(登録商標)の代用物としてのフローラルな付香組成物 |
WO2013062892A1 (en) | 2011-10-25 | 2013-05-02 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
WO2012172122A2 (en) | 2012-06-28 | 2012-12-20 | Lonza Ltd | Method for the preparation of 2-(2,3-dimethylphenyl)-1-propanal |
GB201308236D0 (en) | 2013-05-08 | 2013-06-12 | Givaudan Sa | Improvements in or relating to organic compounds |
GB201308248D0 (en) | 2013-05-08 | 2013-06-12 | Givaudan Sa | Improvements in or relating to organic compounds |
-
2013
- 2013-06-28 WO PCT/CN2013/078376 patent/WO2014205782A1/en active Application Filing
-
2014
- 2014-06-27 JP JP2016522536A patent/JP6438947B2/ja active Active
- 2014-06-27 US US14/900,272 patent/US9708570B2/en active Active
- 2014-06-27 WO PCT/EP2014/063699 patent/WO2014207205A1/en active Application Filing
- 2014-06-27 EP EP14733640.8A patent/EP3013782B1/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2079751A (en) * | 1980-07-09 | 1982-01-27 | Albright & Wilson | Process for the production of alkyl-phenyl propanals and some products thereof |
WO2010091969A1 (en) * | 2009-02-13 | 2010-08-19 | Basf Se | Lily of the valley-type fragrance compositions |
JP2013508331A (ja) * | 2009-10-23 | 2013-03-07 | ビーエーエスエフ ソシエタス・ヨーロピア | 異性化によるm−置換フェニルアルカノールの製造方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021075517A1 (ja) * | 2019-10-17 | 2021-04-22 | 三菱瓦斯化学株式会社 | アルデヒド化合物及びその製造方法、並びに香料組成物 |
WO2023243499A1 (ja) * | 2022-06-17 | 2023-12-21 | 三菱瓦斯化学株式会社 | アルデヒド組成物 |
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WO2014205782A1 (en) | 2014-12-31 |
US20160369205A1 (en) | 2016-12-22 |
EP3013782B1 (en) | 2018-10-03 |
JP6438947B2 (ja) | 2018-12-19 |
US9708570B2 (en) | 2017-07-18 |
EP3013782A1 (en) | 2016-05-04 |
WO2014207205A1 (en) | 2014-12-31 |
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