FR2496652A1 - Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique, leur procede de preparation et leur utilisation comme agents parfumants - Google Patents
Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique, leur procede de preparation et leur utilisation comme agents parfumants Download PDFInfo
- Publication number
- FR2496652A1 FR2496652A1 FR8027271A FR8027271A FR2496652A1 FR 2496652 A1 FR2496652 A1 FR 2496652A1 FR 8027271 A FR8027271 A FR 8027271A FR 8027271 A FR8027271 A FR 8027271A FR 2496652 A1 FR2496652 A1 FR 2496652A1
- Authority
- FR
- France
- Prior art keywords
- radical
- cyclopropane
- methyl
- carbon atoms
- 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.)
- Granted
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- -1 3-SUBSTITUTED CYCLOPROPANE CARBOXYLIC ACID Chemical class 0.000 title claims description 97
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 8
- 239000003795 chemical substances by application Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 241000039077 Copula Species 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical group 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 99
- 229950011148 cyclopropane Drugs 0.000 description 62
- 229910052799 carbon Inorganic materials 0.000 description 60
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 57
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 18
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 16
- 230000035943 smell Effects 0.000 description 13
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 11
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 9
- 239000002304 perfume Substances 0.000 description 9
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 9
- 235000019645 odor Nutrition 0.000 description 8
- YSOKYLAPSSLJTL-UHFFFAOYSA-N 2-ethenyl-1,1-dimethylcyclopropane Chemical compound CC1(C)CC1C=C YSOKYLAPSSLJTL-UHFFFAOYSA-N 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 5
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 5
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 229940067107 phenylethyl alcohol Drugs 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- NFYYLEWFUSSJPZ-UHFFFAOYSA-N 3-but-1-enyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CCC=CC1C(C(O)=O)C1(C)C NFYYLEWFUSSJPZ-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JUPMBRMEHSUGLE-UHFFFAOYSA-N butenyl Chemical compound CCC=[CH] JUPMBRMEHSUGLE-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- TWVXKMAAHORTPL-PLNGDYQASA-N 2,2-dimethyl-3-[(z)-prop-1-enyl]cyclopropane-1-carboxylic acid Chemical compound C\C=C/C1C(C(O)=O)C1(C)C TWVXKMAAHORTPL-PLNGDYQASA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- CAOJXVMGSRHFGB-UHFFFAOYSA-N 3-ethenyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C)C1C(O)=O CAOJXVMGSRHFGB-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- XOLBXXZZQLVKRU-UHFFFAOYSA-N C1CC1.[C] Chemical compound C1CC1.[C] XOLBXXZZQLVKRU-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 244000179970 Monarda didyma Species 0.000 description 2
- 235000010672 Monarda didyma Nutrition 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- SDHXFKBMHSJXHA-UHFFFAOYSA-N 1-carbamoylcyclopropane-1-carboxylic acid Chemical compound NC(=O)C1(C(O)=O)CC1 SDHXFKBMHSJXHA-UHFFFAOYSA-N 0.000 description 1
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- GQWNPIKWYPQUPI-UHFFFAOYSA-N 2-methylbut-3-enoic acid Chemical compound C=CC(C)C(O)=O GQWNPIKWYPQUPI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- OXMWLXYKDKRADR-UHFFFAOYSA-N 3-ethyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CCC1C(C(O)=O)C1(C)C OXMWLXYKDKRADR-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- KFXPOIKSDYRVKS-ARJAWSKDSA-N 4Z-heptenoic acid Chemical compound CC\C=C/CCC(O)=O KFXPOIKSDYRVKS-ARJAWSKDSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
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- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
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- 229940067137 musk ketone Drugs 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- WFNDDSQUKATKNX-UHFFFAOYSA-N phenethyl butyrate Chemical compound CCCC(=O)OCCC1=CC=CC=C1 WFNDDSQUKATKNX-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LDRHVVNCKWGRHQ-UHFFFAOYSA-N propane;propanoic acid Chemical compound CCC.CCC(O)=O LDRHVVNCKWGRHQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Fats And Perfumes (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8027271A FR2496652A1 (fr) | 1980-12-23 | 1980-12-23 | Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique, leur procede de preparation et leur utilisation comme agents parfumants |
| CH8204/81A CH651291A5 (fr) | 1980-12-23 | 1981-12-22 | Drives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique, leur preparation, agents parfumants et compositions les renfermant. |
| IT8149981A IT1172189B (it) | 1980-12-23 | 1981-12-22 | Derivati di acido ciclopropancarbossilico sostituii in posizione 3 da una catena vinilica loro uso procentimento di preparazione loro uso come agenti profumanti e composizioni che li contengono |
| NL8105773A NL8105773A (nl) | 1980-12-23 | 1981-12-22 | 3-vinyl-of vinyleen gesubstitueerde cyclopropaancarbonzuuresters werkwijze voor het bereiden daarvan, en parfums op basis daarvan. |
| GB8138637A GB2091727B (en) | 1980-12-23 | 1981-12-22 | Derivatives of cyclopropane carboxylic acid their preparation their use as perfuming agents and compositions containing them |
| DE19813151210 DE3151210A1 (de) | 1980-12-23 | 1981-12-23 | "neue derivate der in 3-stellung durch eine vinylkette substituierten cyclopropancarbonsaeure, deren herstellung, deren verwendung als duftverleihende mittel und die sie enthaltenden zusammensetzungen" |
| JP56207283A JPS57163345A (en) | 1980-12-23 | 1981-12-23 | Novel derivatives of cyclopropane carboxylic acid substituted by vinyl group at 3 position |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8027271A FR2496652A1 (fr) | 1980-12-23 | 1980-12-23 | Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique, leur procede de preparation et leur utilisation comme agents parfumants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2496652A1 true FR2496652A1 (fr) | 1982-06-25 |
| FR2496652B1 FR2496652B1 (enExample) | 1984-03-16 |
Family
ID=9249373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8027271A Granted FR2496652A1 (fr) | 1980-12-23 | 1980-12-23 | Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique, leur procede de preparation et leur utilisation comme agents parfumants |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS57163345A (enExample) |
| CH (1) | CH651291A5 (enExample) |
| DE (1) | DE3151210A1 (enExample) |
| FR (1) | FR2496652A1 (enExample) |
| GB (1) | GB2091727B (enExample) |
| IT (1) | IT1172189B (enExample) |
| NL (1) | NL8105773A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023036439A1 (en) * | 2021-09-13 | 2023-03-16 | Symrise Ag | Cyclopropanated fragrance compounds |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2185612A1 (enExample) * | 1972-05-25 | 1974-01-04 | Nat Res Dev | |
| DE2437882A1 (de) * | 1973-08-06 | 1975-04-24 | Sumitomo Chemical Co | Verfahren zur herstellung von estern des 3-phenoxybenzylalkohols |
| FR2288733A1 (fr) * | 1973-08-06 | 1976-05-21 | Sumitomo Chemical Co | Nouveaux halogenures d'ammonium quaternaire et leur procede de preparation |
-
1980
- 1980-12-23 FR FR8027271A patent/FR2496652A1/fr active Granted
-
1981
- 1981-12-22 GB GB8138637A patent/GB2091727B/en not_active Expired
- 1981-12-22 CH CH8204/81A patent/CH651291A5/fr not_active IP Right Cessation
- 1981-12-22 IT IT8149981A patent/IT1172189B/it active
- 1981-12-22 NL NL8105773A patent/NL8105773A/nl not_active Application Discontinuation
- 1981-12-23 JP JP56207283A patent/JPS57163345A/ja active Pending
- 1981-12-23 DE DE19813151210 patent/DE3151210A1/de not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2185612A1 (enExample) * | 1972-05-25 | 1974-01-04 | Nat Res Dev | |
| DE2437882A1 (de) * | 1973-08-06 | 1975-04-24 | Sumitomo Chemical Co | Verfahren zur herstellung von estern des 3-phenoxybenzylalkohols |
| FR2288733A1 (fr) * | 1973-08-06 | 1976-05-21 | Sumitomo Chemical Co | Nouveaux halogenures d'ammonium quaternaire et leur procede de preparation |
Non-Patent Citations (4)
| Title |
|---|
| CA1974 * |
| CA1980 * |
| EXBK/76 * |
| EXBK/78 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3151210A1 (de) | 1982-07-22 |
| IT1172189B (it) | 1987-06-18 |
| JPS57163345A (en) | 1982-10-07 |
| CH651291A5 (fr) | 1985-09-13 |
| NL8105773A (nl) | 1982-07-16 |
| GB2091727B (en) | 1985-01-16 |
| FR2496652B1 (enExample) | 1984-03-16 |
| IT8149981A0 (it) | 1981-12-22 |
| GB2091727A (en) | 1982-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |