JP2021531232A - フレグランス物質 - Google Patents
フレグランス物質 Download PDFInfo
- Publication number
- JP2021531232A JP2021531232A JP2020550131A JP2020550131A JP2021531232A JP 2021531232 A JP2021531232 A JP 2021531232A JP 2020550131 A JP2020550131 A JP 2020550131A JP 2020550131 A JP2020550131 A JP 2020550131A JP 2021531232 A JP2021531232 A JP 2021531232A
- Authority
- JP
- Japan
- Prior art keywords
- compounds
- weight
- cis
- fragrance
- fragrance composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003205 fragrance Substances 0.000 title claims abstract description 151
- 239000000126 substance Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 210
- 239000000203 mixture Substances 0.000 claims abstract description 147
- -1 aldehyde compounds Chemical class 0.000 claims description 32
- 241000207199 Citrus Species 0.000 claims description 6
- 241000402754 Erythranthe moschata Species 0.000 claims description 6
- 235000020971 citrus fruits Nutrition 0.000 claims description 6
- SIDBMTXTXXSLIP-XYMCEGRYSA-N C(=C/C\C=C/CC)/C=1SC=CC=1 Chemical compound C(=C/C\C=C/CC)/C=1SC=CC=1 SIDBMTXTXXSLIP-XYMCEGRYSA-N 0.000 claims description 5
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 3
- 235000011613 Pinus brutia Nutrition 0.000 claims description 3
- 241000018646 Pinus brutia Species 0.000 claims description 3
- SIDBMTXTXXSLIP-OONGGIDMSA-N C(=C\C\C=C/CC)/C=1SC=CC=1 Chemical compound C(=C\C\C=C/CC)/C=1SC=CC=1 SIDBMTXTXXSLIP-OONGGIDMSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000006071 cream Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000002304 perfume Substances 0.000 description 9
- 239000002453 shampoo Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 7
- 229940022663 acetate Drugs 0.000 description 7
- 239000006210 lotion Substances 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 235000013769 triethyl citrate Nutrition 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 6
- 239000001069 triethyl citrate Substances 0.000 description 6
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 3
- JFTSYAALCNQOKO-UHFFFAOYSA-N 3-(4-ethylphenyl)-2,2-dimethylpropanal Chemical compound CCC1=CC=C(CC(C)(C)C=O)C=C1 JFTSYAALCNQOKO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000208152 Geranium Species 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 238000003287 bathing Methods 0.000 description 3
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002979 fabric softener Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 3
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- MMFCJPPRCYDLLZ-CMDGGOBGSA-N (2E)-dec-2-enal Chemical compound CCCCCCC\C=C\C=O MMFCJPPRCYDLLZ-CMDGGOBGSA-N 0.000 description 2
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 2
- YPZUZOLGGMJZJO-XRGAULLZSA-N (3as,5as,9as,9br)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1h-benzo[e][1]benzofuran Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@@]2(C)OCC1 YPZUZOLGGMJZJO-XRGAULLZSA-N 0.000 description 2
- MTVBNJVZZAQKRV-DJTWPOEFSA-N (e)-2-methyl-4-[(1r)-2,2,3-trimethylcyclopent-3-en-1-yl]but-2-en-1-ol Chemical compound OCC(/C)=C/C[C@H]1CC=C(C)C1(C)C MTVBNJVZZAQKRV-DJTWPOEFSA-N 0.000 description 2
- RNLHVODSMDJCBR-SOFGYWHQSA-N (e)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C\C1CC=C(C)C1(C)C RNLHVODSMDJCBR-SOFGYWHQSA-N 0.000 description 2
- 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
- NEHPIUGJDUWSRR-UHFFFAOYSA-N 1-(4-propan-2-ylcyclohexyl)ethanol Chemical compound CC(C)C1CCC(C(C)O)CC1 NEHPIUGJDUWSRR-UHFFFAOYSA-N 0.000 description 2
- MVTYXAVPKZRAMW-UHFFFAOYSA-N 1-methyl-4-(4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)CCCC1=CCC(C)(C=O)CC1 MVTYXAVPKZRAMW-UHFFFAOYSA-N 0.000 description 2
- HMWPDRYGIBLSHB-UHFFFAOYSA-N 17-oxacycloheptadec-6-en-1-one Chemical compound O=C1CCCCC=CCCCCCCCCCO1 HMWPDRYGIBLSHB-UHFFFAOYSA-N 0.000 description 2
- PUKWIVZFEZFVAT-UHFFFAOYSA-N 2,2,5-trimethyl-5-pentylcyclopentan-1-one Chemical compound CCCCCC1(C)CCC(C)(C)C1=O PUKWIVZFEZFVAT-UHFFFAOYSA-N 0.000 description 2
- JEPWTUCYPWOCQV-UHFFFAOYSA-N 2,4-dimethyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-dioxolane Chemical compound O1C(C)COC1(C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 JEPWTUCYPWOCQV-UHFFFAOYSA-N 0.000 description 2
- GPVOTKFXWGURGP-UHFFFAOYSA-N 2,5,5-trimethyl-1,3,4,4a,6,7-hexahydronaphthalen-2-ol Chemical compound C1C(C)(O)CCC2C1=CCCC2(C)C GPVOTKFXWGURGP-UHFFFAOYSA-N 0.000 description 2
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical compound CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 2
- HGDVHRITTGWMJK-UHFFFAOYSA-N 2,6-dimethylheptan-2-ol Chemical compound CC(C)CCCC(C)(C)O HGDVHRITTGWMJK-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- KFBPVHFUHYKWIF-UHFFFAOYSA-N 2-propan-2-yloxyethyl 2-hydroxybenzoate Chemical compound CC(C)OCCOC(=O)C1=CC=CC=C1O KFBPVHFUHYKWIF-UHFFFAOYSA-N 0.000 description 2
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- MCWLALJQNGOMTG-LMJRQTCTSA-N C(=C/C=C/CCC)/C=1SC=CC=1 Chemical compound C(=C/C=C/CCC)/C=1SC=CC=1 MCWLALJQNGOMTG-LMJRQTCTSA-N 0.000 description 2
- SIDBMTXTXXSLIP-MVJHVNNNSA-N C(=C/C\C=C\CC)/C=1SC=CC=1 Chemical group C(=C/C\C=C\CC)/C=1SC=CC=1 SIDBMTXTXXSLIP-MVJHVNNNSA-N 0.000 description 2
- SIDBMTXTXXSLIP-PBOULFJWSA-N C(=C\C\C=C\CC)/C=1SC=CC=1 Chemical group C(=C\C\C=C\CC)/C=1SC=CC=1 SIDBMTXTXXSLIP-PBOULFJWSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- CYHBDKTZDLSRMY-UHFFFAOYSA-N Hexyl 2-methylpropanoate Chemical compound CCCCCCOC(=O)C(C)C CYHBDKTZDLSRMY-UHFFFAOYSA-N 0.000 description 2
- 206010021639 Incontinence Diseases 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- UUQHKWMIDYRWHH-UHFFFAOYSA-N Methyl beta-orcinolcarboxylate Chemical compound COC(=O)C1=C(C)C=C(O)C(C)=C1O UUQHKWMIDYRWHH-UHFFFAOYSA-N 0.000 description 2
- LQKRYVGRPXFFAV-UHFFFAOYSA-N Phenylmethylglycidic ester Chemical compound CCOC(=O)C1OC1(C)C1=CC=CC=C1 LQKRYVGRPXFFAV-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 2
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 2
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 2
- 230000001166 anti-perspirative effect Effects 0.000 description 2
- 239000003213 antiperspirant Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MMFCJPPRCYDLLZ-UHFFFAOYSA-N dec-2-enal Natural products CCCCCCCC=CC=O MMFCJPPRCYDLLZ-UHFFFAOYSA-N 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- HCRBXQFHJMCTLF-ZCFIWIBFSA-N ethyl (2r)-2-methylbutanoate Chemical compound CCOC(=O)[C@H](C)CC HCRBXQFHJMCTLF-ZCFIWIBFSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-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
- 238000011156 evaluation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 2
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- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
- UODXCYZDMHPIJE-UHFFFAOYSA-N menthanol Chemical compound CC1CCC(C(C)(C)O)CC1 UODXCYZDMHPIJE-UHFFFAOYSA-N 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- ALHUZKCOMYUFRB-UHFFFAOYSA-N muskone Natural products CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 2
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- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 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
- RUMOYJJNUMEFDD-UHFFFAOYSA-N perillyl aldehyde Chemical compound CC(=C)C1CCC(C=O)=CC1 RUMOYJJNUMEFDD-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 238000012549 training Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
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- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000015041 whisky Nutrition 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3481—Organic compounds containing sulfur containing sulfur in a heterocyclic ring, e.g. sultones or sulfolanes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
Description
本出願は、2018年6月4日に出願された米国仮特許出願第62/680,403号に対する優先権を主張するものであり、その内容全体を参照により本明細書に援用する。
本出願は、フレグランス組成物中のフレグランス成分として有用な化合物に関する。
したがって、ユニークなフレグランス化合物の必要性と需要が依然として存在している。また、多様な消費者製品に使用するために、心地よく消費者に好まれる香りプロファイルを有するフレグランス組成物が必要とされている。
ある態様において、本明細書に開示された主題は、式Iにより表される化合物を提供する。
本開示のある態様において、フレグランス組成物は、式Iの化合物のシス−シス異性体およびシス−トランス異性体の約50/50の混合物を含み得る。
1. 定義
2. フレグランス化合物
3. フレグランス組成物
4. 消費者製品におけるフレグランス組成物の使用
本明細書で使用される用語は、一般に、本開示の文脈において、および各用語が使用される特定の文脈において、当該技術分野における通常の意味を有する。本開示の化合物、組成物および方法、ならびにそれらの製造および使用方法を記載する上でさらなるガイダンスを当業者に提供するために、特定の用語が下文において、または本明細書の他の箇所で後述されている。
本明細書において、単語「a」または「an」の使用は、請求項および/または明細書において用語「含む(comprising)」と併せて使用される場合、「1つ」を意味し得るが、それはまた「1つ以上」、「少なくとも1つ」、「複数」、および「1つまたは1つより多い」の意味とも一致する。さらに、用語「有する(having)」、「含む(including)」、「含む(containing)」および「含む(comprising)」は互換性があり、当業者は、これらの用語がオープンエンド用語であることを認識している。
本明細書中で使用される場合、用語「消費者製品」または「最終製品」は、市販された表示にて消費者が使用することができる状態になっている組成物を指す。消費者製品中での使用に適した溶媒とは、最終製品の他の成分と組み合わされた場合に、所期の消費者使用に不適切な消費者製品をもたらすことのない溶媒である。
本開示は、ユニークで求められる芳香特性を有するフレグランス化合物の合成およびアプリケーションに関する。
特定の実施態様では、本明細書に開示された主題は式Iの化合物を提供する。
特定の実施態様では、上記化合物は、フレグランス組成物として提供され得る。本開示の主題の特定の実施形態は、有効量の式Iの化合物をフレグランス組成物に添加することにより、そのフレグランス組成物の香り特性を改質、増強または改善する方法を提供する。一実施形態においては、式Iの化合物のシス−シス異性体およびトランス−シス異性体の約50/50混合物をフレグランス組成物中で使用することができる。特定の実施形態では、フレグランス組成物は、2−((1Z,4Z)−ヘプタ−1,4−ジエン−1−イル)チオフェンおよび2−((1E,4Z)−ヘプタ−1,4−ジエン−1−イル)チオフェンの約50/50混合物を含み得る。
特定の実施形態では、本開示のフレグランス組成物は、消費者製品の一部として調合することができる。このような消費者製品は、配合者が選択する任意の方法により、任意の適切な形態で調製することができる。本開示の主題の化合物を含むことができる適切な消費者製品には、これらに限定されないが、エアケア製品(例えば、キャンドル、エアロゾル、芳香剤、室内スプレーおよびミスト、液体電気式芳香剤、芳香拡散器、ゲル状芳香剤、プラグイン芳香剤およびオイル、ワックス溶融物など);ベビーケア製品(例えば、成人失禁用衣料、よだれかけ、おむつ、トレーニングパンツ、乳幼児用および幼児用ケアワイパーを含む使い捨て吸収性および/または非吸収性物品に関連する消費者製品;および手洗い石鹸、シャンプー、ローション、シャワーゲル、および衣類を含むパーソナルケア製品);ファブリックケアおよびホームケア製品(例えば、ファブリックコンディショナー(ソフナーを含む)、洗濯用洗剤、洗濯用およびリンス用添加剤および/またはケア、漂白剤、乾燥機シート、香りづけビーズ、食器洗浄剤、ハードサーフェスクリーナーおよび/またはトリートメント、ならびに、家庭用および/または業務用のその他洗浄剤などの消費者製品);パーソナルケア製品 (例えば、ローション、クリーム、保湿剤、ボディウォッシュ、ハンドソープ、シャンプー、コンディショナー、石鹸など);ファミリーケア製品(例えば、ウェットまたはドライバスティッシュ、フェイシャルティッシュ、使い捨てハンカチ、使い捨てタオルおよび/またはワイプ、タオル、トイレットペーパー、ティッシュペーパー、ウェットタオルなど);女性ケア製品(例えば、生理用パッド、失禁用パッド、陰唇間用パッド、パンティーライナー、ペッサリー、生理用ナプキン、タンポンおよびタンポン用アプリケーターおよび/またはワイプなど);セクシュアルケア製品(例えば、潤滑剤およびコンドームなどのセクシュアルエイドまたはセクシュアルヘルスに関連する製品);ペットケア製品(例えば、ペット臭用猫砂、ペットデオドライザー、ペットフード、おやつ、その他の経口送達製品を含むペットの健康および栄養に関連する製品、グルーミング用補助具、シャンプー、スタイリング剤、コンディショナーを含むペットヘア/ファーを処理するための製品、消臭剤および制汗剤、石鹸、クリーム、ローションおよびその他の局所適用製品を含むペットの肌用クレンジングまたはトリートメント用製品、トレーニング用補助具、玩具及び診断技術;ファインフレグランス(パルファム、エクストレドパルファム、オーデパルファム、パルファムドトワレ、オードトワレ、オーデコロン、ボディスプラッシュ、アフターシェイブ、ベビーコロンを含むボディミストなどのパフュームオイルの含水アルコール溶液を含む);カーケア製品(例えば、クリーナー、芳香剤、ワイプ、石鹸等);化粧品(例えば、スキンクリーム、クレンジングクリーム、ナイトクリーム、ハンドクリーム、ローション、アフターシェイブローション、ボディローション、ファンデーション、リップスティック、リップクリーム、ネイルポリッシュ、ネイルポリッシュリムーバー、タルカムパウダー、アンチリンクルおよび/またはアンチエイジング化粧品、日焼け止め製品、マッサージオイルなど);ビューティーケア(例えば、シャンプー、スタイリング剤、コンディショナーなどの人の毛髪を処理するための製品、消臭剤および制汗剤、パーソナルクレンジング用製品、クリーム、ローション、およびその他の局所適用製品の適用を含む人の皮膚を処理するための製品、シェービング、リンス、リンスインシャンプーといった製品、ポマード、ヘアトニック、ヘアジェル、ヘアクリーム、およびヘアムースなどのヘアスタイリング剤、育毛剤、染毛剤など);入浴剤(例えば、粉末入浴剤、固形発砲入浴剤、バスオイル、バブルバスアロマジェネレーター、バスソルトなど);脱毛製品(例えば、脱毛クリーム、シュガーペーストまたはジェル、ワックスを含む脱毛用の製品);および、局所用医薬品(例えば、ヒトおよび/または動物の疾病の治療および/または緩和に使用される軟膏、クリームなど)が含まれる。いくつかの最終製品中に存在し得る溶媒に応じて、例えば、カプセル化または安定剤との併用、または当業者に周知の他の方法によって、化合物を早期劣化から保護する必要があり得る。本開示のある態様において、フレグランス組成物は、消費者製品の総重量を基準にして、組成物が約0.0001重量%から約90重量%、または約0.001重量%から約75重量%、または約1重量%から約50重量%、または約5重量%から約25重量%、または約10重量%から約15重量%の量、およびその間の値で存在する消費者製品と混合することができる。他の実施形態において、フレグランス組成物は、消費者製品の総重量を基準にして、組成物が約0.0001重量%から約10重量%、または約0.001重量%から約5重量%、または約0.001重量%から約1重量%の量で存在する消費者製品と混合することができる。
他の実施形態では、消費者製品は、消費者製品の総重量に基づいて、フレグランス組成物を、約90重量%から約100重量%まで、または約95重量%から約100重量%まで、または約99重量%から約100重量%まで含み得る。特定の実施形態では、消費者製品は、消費者製品の総重量に基づいて、フレグランス組成物を、約90%、約95%、約99%、または約100%含み得る。
当該実施例の使用は、例示的なものにすぎず、開示された主題事項または例示的な用語の範囲および意味を制限するものではない。同様に、開示された主題は、本明細書に記載されたいずれかの特定の好ましい実施形態に限定されない。実際、本明細書を読むことによって、開示された主題の多くの改変形態および変更形態が、当業者に明らかである。したがって、開示された主題は、特許請求の範囲が権利を有する均等物の全範囲と併せて、別記の特許請求の範囲の用語によってのみ限定される。
以下の実施例は、本開示の特定の実施形態として提供され、ここで、略語は当該技術分野において通常の意味を有する。温度は摂氏(℃)で示し、NMRスペクトルデータは1Hおよび13Cについて400 MHz装置を用いてCDCl3中で記録し、化学シフトはTMSを標準としてppmで示す。
式Iの化合物を以下のように合成した:
ウィッティヒ塩 シス−3−ヘキセニルトリフェニルホスホニウムブロマイド (62.4 g、1.1当量)を滴下漏斗を備えたフラスコに投入した。次いで、フラスコを窒素でパージしフラッシュした。無水ジエチルエーテル (360mL)を塩に添加し、スラリーを形成した。N−BuLi (ヘキサン中2.5 M、58.8 ml、1.1当量)を室温で滴下して添加した。添加完了後、反応混合物を1時間撹拌して、イリドを形成した。次いで、反応混合物をアセトンおよびドライアイススラリーの浴中で約−35℃で冷却した。無水ジエチルエーテル135 mL中のチオフェンカルボキシアルデヒド (15 g、1当量)を冷却した反応混合物に滴下した。添加後、反応物を徐々に室温まで温め、室温で一晩撹拌した。その後、反応混合物を飽和NH4Clでクエンチし、ジエチルエーテルで抽出し、食塩水で洗浄し、MgSO4で乾燥し、濾過した。次いで濾液を濃縮した。生成したトリフェニルホスフィンオキシドの大部分を沈殿させるために、ジエチルエーテルを粗生成物に添加した。懸濁液を濾過し、濾液を真空下で濃縮した。次いで、クーゲルロール蒸留により、生成物 (シス−シスおよびトランス−シス異性体の50/50混合物として)を残りのトリフェニルホスフィンオキシド (14.0g、収率57%)から分離した。本品はグリーン、トマト、バイオレットリーフ、ゼラニウムの香調を有する。GC/MS(EI): m/z(%) 178(28)、163(6)、149(51)、135(52)、123(15)、110(100)、97(69)、79(39)、65(22)、45(56) 1 H NMR (CDCl3): δ .09(t、3H)、2.08(m、2H)、2.89/3.13(t、2H)、5.51(vinyl m、3H)、6.05/6.48(vinyl m、1H)、6.97(m、2H)、7.25(m、1H)
シャンプーにおける使用を実証するために、本明細書に開示されている化合物からベリーフレグランス組成物を調製した。この実施例において、本明細書に開示された化合物は、式Iの化合物のシス−シスおよびシス−トランス異性体の50/50混合物である。本明細書に開示された化合物は、10%TEC希釈物として、次いで、DPG中の10%希釈物にさらに希釈された。本開示の化合物を含むフレグランス組成物を表1に示す。
柔軟剤における使用を実証するために、本明細書に開示されている化合物からピーチフレグランス組成物を調製した。この実施例において、本明細書に開示された化合物は、式Iの化合物のシス−シスおよびシス−トランス異性体の50/50混合物である。本明細書に開示された化合物は、10%TEC希釈物である。
開示された主題の精神または範囲から逸脱することなく、開示された主題の装置、方法、およびシステムにおいて種々の修正および変更ができることは、当業者には明らかであろう。したがって、開示された主題は、別記の特許請求の範囲およびそれらの同等の範囲内の修正および変更を含むことが意図されている。
本出願全体を通して引用される任意の特許、特許出願、刊行物、製品説明書、およびプロトコルは、そのすべての開示を、あらゆる目的のために、参照によりその全体が本明細書に組み込まれる。
Claims (7)
- 請求項1に記載の化合物を含むフレグランス組成物。
- 請求項1に記載の化合物のシス−シス異性体およびシス−トランス異性体の約50/50の混合物を含むフレグランス組成物。
- 前記組成物が、2−((1Z,4Z)−ヘプタ−1,4−ジエン−1−イル)チオフェンおよび2−((1E,4Z)−ヘプタ−1,4−ジエン−1−イル)チオフェンの約50/50混合物を含む、請求項2または3に記載のフレグランス組成物。
- 式Iの化合物が、フレグランス組成物の総重量に基づいて、約0.01重量%から約20重量%の量で存在する、請求項2または3に記載のフレグランス組成物。
- 1つまたは複数のアルデヒド系化合物、1つまたは複数のアニマリック系化合物、1つまたは複数のバルサミック系化合物、1つまたは複数のシトラス系化合物、1つまたは複数のフローラル系化合物、1つまたは複数のフルーティー系化合物、1つまたは複数のグルマン系化合物、1つまたは複数のハーブ系化合物、1つまたは複数のモス系化合物、1つまたは複数のムスク系化合物、1つまたは複数の松系化合物、1つまたは複数のパウダリー系化合物、1つまたは複数のスパイシー系化合物、および/または1つまたは複数のウッディー系および/またはアンバー系化合物、およびそれらの組み合わせからなる群から選択される1つまたは複数の化合物をさらに含む、請求項2または3に記載のフレグランス組成物。
- 請求項1に記載の化合物または請求項2または3に記載の組成物を含む消費者製品。
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PCT/US2019/035367 WO2019236562A1 (en) | 2018-06-04 | 2019-06-04 | Fragrance materials |
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US2666765A (en) * | 1949-12-10 | 1954-01-19 | Universal Oil Prod Co | Production of alkenylthiophenes |
US6867323B2 (en) * | 2000-06-06 | 2005-03-15 | The Board Of Trustees Of The University Of Illinois | Cross-coupling reaction of organosilicon nucleophiles |
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