CA2313337A1 - Cyclopentylalkyl-nitriles - Google Patents
Cyclopentylalkyl-nitriles Download PDFInfo
- Publication number
- CA2313337A1 CA2313337A1 CA002313337A CA2313337A CA2313337A1 CA 2313337 A1 CA2313337 A1 CA 2313337A1 CA 002313337 A CA002313337 A CA 002313337A CA 2313337 A CA2313337 A CA 2313337A CA 2313337 A1 CA2313337 A1 CA 2313337A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- mmol
- cyclopentyl
- compound
- yield
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 239000003205 fragrance Substances 0.000 claims abstract description 24
- -1 and R2 is H Chemical group 0.000 claims abstract description 19
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims abstract description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims abstract description 6
- 125000006193 alkinyl group Chemical group 0.000 claims abstract description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 10
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 2
- NVKDEKYWTQXNHG-UHFFFAOYSA-N 5-cyclopentylhexanenitrile Chemical compound N#CCCCC(C)C1CCCC1 NVKDEKYWTQXNHG-UHFFFAOYSA-N 0.000 claims description 7
- IXZYGBIGKWQGGG-UHFFFAOYSA-N 5-cyclopentylidenehexanenitrile Chemical compound N#CCCCC(C)=C1CCCC1 IXZYGBIGKWQGGG-UHFFFAOYSA-N 0.000 claims description 4
- DMYRODGWGFMICN-UHFFFAOYSA-N 4-cyclopentylpentanenitrile Chemical compound N#CCCC(C)C1CCCC1 DMYRODGWGFMICN-UHFFFAOYSA-N 0.000 claims description 2
- DKNBYQDPXXREEZ-UHFFFAOYSA-N 5-(cyclopenten-1-yl)hexanenitrile Chemical compound N#CCCCC(C)C1=CCCC1 DKNBYQDPXXREEZ-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- PXBZLPOUZUBEKE-UHFFFAOYSA-N 5-cyclopentyl-3-methylpentanenitrile Chemical compound N#CCC(C)CCC1CCCC1 PXBZLPOUZUBEKE-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 12
- 239000000243 solution Substances 0.000 description 30
- 235000019645 odor Nutrition 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 25
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 239000012267 brine Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- PQJPDBXYUUFDRK-UHFFFAOYSA-N 5-cyclopentylidenepentan-2-one Chemical compound CC(=O)CCC=C1CCCC1 PQJPDBXYUUFDRK-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 238000005481 NMR spectroscopy Methods 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
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 241000207199 Citrus Species 0.000 description 5
- 235000015164 Iris germanica var. florentina Nutrition 0.000 description 5
- 240000004101 Iris pallida Species 0.000 description 5
- 235000015265 Iris pallida Nutrition 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 235000020971 citrus fruits Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- ZJCKWOJXOPMEIC-UHFFFAOYSA-N 4-cyclopentylpentanoic acid Chemical compound OC(=O)CCC(C)C1CCCC1 ZJCKWOJXOPMEIC-UHFFFAOYSA-N 0.000 description 4
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
- 240000007436 Cananga odorata Species 0.000 description 4
- 235000009046 Convallaria majalis Nutrition 0.000 description 4
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 241000208152 Geranium Species 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229930002839 ionone Natural products 0.000 description 4
- 150000002499 ionone derivatives Chemical class 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- AJMGTRVUGVDVBN-UHFFFAOYSA-N 5-cyclopentyl-5-hydroxyhexanenitrile Chemical compound N#CCCCC(O)(C)C1CCCC1 AJMGTRVUGVDVBN-UHFFFAOYSA-N 0.000 description 3
- LHWCGANJGDSRAO-UHFFFAOYSA-N 5-cyclopentylhexanal Chemical compound O=CCCCC(C)C1CCCC1 LHWCGANJGDSRAO-UHFFFAOYSA-N 0.000 description 3
- UPWJIBBATZBVAV-UHFFFAOYSA-N 5-cyclopentylidenepentan-2-yl propanoate Chemical compound CCC(=O)OC(C)CCC=C1CCCC1 UPWJIBBATZBVAV-UHFFFAOYSA-N 0.000 description 3
- QQYHZGKDXBXAQZ-UHFFFAOYSA-N 5-cyclopentylpentan-2-one Chemical compound CC(=O)CCCC1CCCC1 QQYHZGKDXBXAQZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 244000099147 Ananas comosus Species 0.000 description 3
- 235000007119 Ananas comosus Nutrition 0.000 description 3
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 3
- 241001672694 Citrus reticulata Species 0.000 description 3
- 244000068485 Convallaria majalis Species 0.000 description 3
- 235000007129 Cuminum cyminum Nutrition 0.000 description 3
- 244000304337 Cuminum cyminum Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002781 deodorant agent Substances 0.000 description 3
- QNAQZOWKDCZUMY-UHFFFAOYSA-N ethyl 5-cyclopentyl-3-methylpent-4-enoate Chemical compound CCOC(=O)CC(C)C=CC1CCCC1 QNAQZOWKDCZUMY-UHFFFAOYSA-N 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- JSQRFMSSEXQLTC-UHFFFAOYSA-N 1-ethenylcyclopentan-1-ol Chemical compound C=CC1(O)CCCC1 JSQRFMSSEXQLTC-UHFFFAOYSA-N 0.000 description 2
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- WJFMFQSDFHVJDE-UHFFFAOYSA-N 4-cyclopentylpentanal Chemical compound O=CCCC(C)C1CCCC1 WJFMFQSDFHVJDE-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- KBSPSKDTOFIEFA-UHFFFAOYSA-N 5-(cyclopenten-1-yl)pentan-2-one Chemical compound CC(=O)CCCC1=CCCC1 KBSPSKDTOFIEFA-UHFFFAOYSA-N 0.000 description 2
- AYQIQACXWFBWBQ-UHFFFAOYSA-N 5-cyclopentylidene-2-methylpentan-2-ol Chemical compound CC(C)(O)CCC=C1CCCC1 AYQIQACXWFBWBQ-UHFFFAOYSA-N 0.000 description 2
- 240000001851 Artemisia dracunculus Species 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 241000234269 Liliales Species 0.000 description 2
- ZYEMGPIYFIJGTP-UHFFFAOYSA-N O-methyleugenol Chemical compound COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 240000002505 Pogostemon cablin Species 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 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
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- 238000009792 diffusion process Methods 0.000 description 2
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- 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
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- DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 1
- WSTQLNQRVZNEDV-CSKARUKUSA-N (e)-4-methyldec-3-en-5-ol Chemical compound CCCCCC(O)C(\C)=C\CC WSTQLNQRVZNEDV-CSKARUKUSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
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- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- RBAUBIIMPLZNGC-UHFFFAOYSA-N methyl 2-[[3-(4-tert-butylphenyl)-2-methylpropylidene]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N=CC(C)CC1=CC=C(C(C)(C)C)C=C1 RBAUBIIMPLZNGC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YAHNYLGSSPTTAG-UHFFFAOYSA-N methyl n-(3,4-dichlorophenyl)carbamodithioate Chemical compound CSC(=S)NC1=CC=C(Cl)C(Cl)=C1 YAHNYLGSSPTTAG-UHFFFAOYSA-N 0.000 description 1
- PRHTXAOWJQTLBO-UHFFFAOYSA-N methyleugenol Natural products COC1=CC=C(C(C)=C)C=C1OC PRHTXAOWJQTLBO-UHFFFAOYSA-N 0.000 description 1
- 229940116837 methyleugenol Drugs 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001627 myristica fragrans houtt. fruit oil Substances 0.000 description 1
- LLRCQKLPJLNYLV-UHFFFAOYSA-N n-(5-cyclopentyl-3-methylpentylidene)hydroxylamine Chemical compound ON=CCC(C)CCC1CCCC1 LLRCQKLPJLNYLV-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- LVECZGHBXXYWBO-UHFFFAOYSA-N pentadecanolide Natural products CC1CCCCCCCCCCCCC(=O)O1 LVECZGHBXXYWBO-UHFFFAOYSA-N 0.000 description 1
- OHIDOYVJPZRAHI-UHFFFAOYSA-N pentanenitrile Chemical compound CC[CH]CC#N OHIDOYVJPZRAHI-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 229930194459 prunolide Natural products 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 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
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- WXETUDXXEZHSCS-MAVITOTKSA-N vertofix coeur Chemical compound C[C@@H]1CC[C@@]2(C(/CC3)=C\C(C)=O)[C@@H]3C(C)(C)[C@@H]1C2 WXETUDXXEZHSCS-MAVITOTKSA-N 0.000 description 1
- YEIGUXGHHKAURB-UHFFFAOYSA-N viridine Natural products O=C1C2=C3CCC(=O)C3=CC=C2C2(C)C(O)C(OC)C(=O)C3=COC1=C23 YEIGUXGHHKAURB-UHFFFAOYSA-N 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic 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
- 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
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Ceramic Products (AREA)
- Polyurethanes Or Polyureas (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99810585.2 | 1999-07-05 | ||
| EP99810585 | 1999-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2313337A1 true CA2313337A1 (en) | 2001-01-05 |
Family
ID=8242905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002313337A Abandoned CA2313337A1 (en) | 1999-07-05 | 2000-07-04 | Cyclopentylalkyl-nitriles |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US6410000B1 (enExample) |
| JP (1) | JP2001048854A (enExample) |
| CN (1) | CN1147467C (enExample) |
| AT (1) | ATE263143T1 (enExample) |
| AU (1) | AU742027B2 (enExample) |
| BR (1) | BR0002448A (enExample) |
| CA (1) | CA2313337A1 (enExample) |
| DE (1) | DE60009394T2 (enExample) |
| ES (1) | ES2216757T3 (enExample) |
| SG (1) | SG109422A1 (enExample) |
| ZA (1) | ZA200002400B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2579957A (en) * | 1947-10-30 | 1951-12-25 | Frederic A Pearne | Vacuum header for combine harvesters |
| GB0031047D0 (en) * | 2000-12-20 | 2001-01-31 | Quest Int | Perfume compositions |
| US7763238B2 (en) * | 2002-01-16 | 2010-07-27 | Monell Chemical Senses Center | Olfactory adaptation and cross-adapting agents to reduce the perception of body odors |
| JPWO2005087703A1 (ja) * | 2004-03-12 | 2008-01-24 | 日本ゼオン株式会社 | エステル化合物、香料組成物及びエステル化合物の製造方法 |
| KR100744823B1 (ko) * | 2006-02-15 | 2007-08-01 | 한국과학기술연구원 | (2-시클로펜테닐)클로로실란 유도체와 이의 제조방법 |
| WO2008068310A1 (en) * | 2006-12-08 | 2008-06-12 | V. Mane Fils | Use of campholenic derivatives as fragrant ingredients in perfumery and flavouring |
| ES2623004T3 (es) | 2010-08-25 | 2017-07-10 | Kedar Ramesh Vaze | Composiciones de perfumería y síntesis de una sustancia odorífera |
| FR2975283B1 (fr) | 2011-05-17 | 2019-04-05 | V. Mane Fils | Utilisation sensorielle des derives du 6-cyclopentylidenehexane |
| GB201115409D0 (en) * | 2011-09-07 | 2011-10-19 | Givaudan Sa | Organic compounds |
| ES2656146T3 (es) * | 2012-02-09 | 2018-02-23 | Firmenich Sa | Aldehídos como ingredientes perfumantes |
| ES2627567T3 (es) | 2012-12-26 | 2017-07-28 | Kao Corporation | Compuesto de nitrilo, método de preparación del mismo, y composición de fragancia que comprende el compuesto de nitrilo |
| WO2015034084A1 (ja) * | 2013-09-06 | 2015-03-12 | 高砂香料工業株式会社 | 香料組成物 |
| US11479739B2 (en) * | 2018-10-30 | 2022-10-25 | Firmenich Sa | Cyclic oxy ether compounds as perfuming ingredients |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS171102B1 (en) * | 1973-09-20 | 1976-10-31 | Ludvik Streinz | Insecticide and method of active substance preparationt |
| CH616077A5 (enExample) | 1976-06-30 | 1980-03-14 | Firmenich & Cie | |
| JPS55127316A (en) | 1979-03-26 | 1980-10-02 | Nippon Zeon Co Ltd | Perfume composition |
| GB2053199B (en) * | 1979-05-09 | 1983-07-06 | Polak S Frutal Work Bv | Nitriles and their use as perfume chemicals |
| ES2138688T3 (es) | 1994-07-28 | 2000-01-16 | Firmenich & Cie | Derivados de aldehido camfolenico y su utilizacion en perfumeria. |
| EP0770671B1 (en) | 1995-11-03 | 1999-09-22 | Quest International B.V. | Cyclopentylidene-cyclopentanol in perfumery |
| JP3400291B2 (ja) * | 1996-09-17 | 2003-04-28 | 高砂香料工業株式会社 | （ｅ）−（ｒ）−２−アルキル−４−（２，２，３−トリメチルシクロペント−３−エン−１−イル）−２−ブテン−１−オール誘導体、その製造方法および用途 |
| EP0913383B1 (en) * | 1997-10-29 | 2001-09-05 | Givaudan SA | New spirocyclic compounds |
-
2000
- 2000-05-12 ES ES00110015T patent/ES2216757T3/es not_active Expired - Lifetime
- 2000-05-12 AT AT00110015T patent/ATE263143T1/de not_active IP Right Cessation
- 2000-05-12 DE DE60009394T patent/DE60009394T2/de not_active Expired - Lifetime
- 2000-05-16 ZA ZA200002400A patent/ZA200002400B/xx unknown
- 2000-05-31 SG SG200003033A patent/SG109422A1/en unknown
- 2000-06-06 AU AU37965/00A patent/AU742027B2/en not_active Ceased
- 2000-07-03 CN CNB001199293A patent/CN1147467C/zh not_active Expired - Fee Related
- 2000-07-04 JP JP2000201718A patent/JP2001048854A/ja active Pending
- 2000-07-04 CA CA002313337A patent/CA2313337A1/en not_active Abandoned
- 2000-07-05 BR BR0002448-1A patent/BR0002448A/pt not_active IP Right Cessation
- 2000-07-05 US US09/609,845 patent/US6410000B1/en not_active Expired - Fee Related
-
2001
- 2001-12-31 US US10/038,735 patent/US6399811B1/en not_active Expired - Fee Related
-
2002
- 2002-04-12 US US10/121,519 patent/US6441052B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6441052B1 (en) | 2002-08-27 |
| BR0002448A (pt) | 2001-03-13 |
| DE60009394D1 (de) | 2004-05-06 |
| ZA200002400B (en) | 2000-11-16 |
| ATE263143T1 (de) | 2004-04-15 |
| SG109422A1 (en) | 2005-03-30 |
| AU3796500A (en) | 2001-04-26 |
| DE60009394T2 (de) | 2005-02-24 |
| JP2001048854A (ja) | 2001-02-20 |
| CN1290691A (zh) | 2001-04-11 |
| US6399811B1 (en) | 2002-06-04 |
| US20020086901A1 (en) | 2002-07-04 |
| ES2216757T3 (es) | 2004-11-01 |
| CN1147467C (zh) | 2004-04-28 |
| AU742027B2 (en) | 2001-12-13 |
| US6410000B1 (en) | 2002-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |