NL8204355A - Nieuwe cyclopropaanverbindingen, werkwijze voor hun bereiding, hun toepassing als reukstoffen en samenstellingen, die hen bevatten. - Google Patents

Nieuwe cyclopropaanverbindingen, werkwijze voor hun bereiding, hun toepassing als reukstoffen en samenstellingen, die hen bevatten. Download PDF

Info

Publication number: NL8204355A
Authority: NL; Netherlands
Prior art keywords: methyl; group; propenyl; dimethyl; formula
Prior art date: 1981-11-10

Application number

NL8204355A

Other languages

English (en)

Dutch (nl)

Original Assignee

Roussel Uclaf

Priority date (The priority date 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 date listed.)

1981-11-10

Filing date

1982-11-10

Publication date

1983-06-01

1982-11-10 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1983-06-01 Publication of NL8204355A publication Critical patent/NL8204355A/nl

Links

239000000203 mixture Substances 0.000 title claims description 14
239000002304 perfume Substances 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 4
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 title description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 144
125000006020 2-methyl-1-propenyl group Chemical group 0.000 claims description 73
125000000217 alkyl group Chemical group 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000000304 alkynyl group Chemical group 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000000468 ketone group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000001602 bicycloalkyls Chemical group 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
229940049953 phenylacetate Drugs 0.000 claims description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 3
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
238000003556 assay Methods 0.000 claims 1
125000004474 heteroalkylene group Chemical group 0.000 claims 1
125000004475 heteroaralkyl group Chemical group 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
-1 cyclopropane compound Chemical class 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
240000008790 Musa x paradisiaca Species 0.000 description 13
235000018290 Musa x paradisiaca Nutrition 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
HIPIENNKVJCMAP-UHFFFAOYSA-N trans-chrysanthemyl alcohol Natural products CC(C)=CC1C(CO)C1(C)C HIPIENNKVJCMAP-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
235000019645 odor Nutrition 0.000 description 5
239000000243 solution Substances 0.000 description 5
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
229950011148 cyclopropane Drugs 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
125000006017 1-propenyl group Chemical group 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000012459 cleaning agent Substances 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229940017219 methyl propionate Drugs 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000344 soap Substances 0.000 description 3
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
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
229960000956 coumarin Drugs 0.000 description 2
235000001671 coumarin Nutrition 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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 2
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000003205 fragrance Substances 0.000 description 2
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
229940095102 methyl benzoate Drugs 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000010679 vetiver oil Substances 0.000 description 2
GFDFZTFQPIBNSQ-UHFFFAOYSA-N (+)-homo-18-epiormosanine Natural products C1C(C23)CCCN3CN3CCCCC3C32CN2CCCCC2C1C3 GFDFZTFQPIBNSQ-UHFFFAOYSA-N 0.000 description 1
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
JRJBVWJSTHECJK-LUAWRHEFSA-N (z)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one Chemical compound CC(=O)C(\C)=C/C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-LUAWRHEFSA-N 0.000 description 1
CWBXRPMPOBUVMH-UHFFFAOYSA-N 1-cyclopropylbutan-2-one Chemical compound CCC(=O)CC1CC1 CWBXRPMPOBUVMH-UHFFFAOYSA-N 0.000 description 1
125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
LUNMJRJMSXZSLC-UHFFFAOYSA-N 2-cyclopropylethanol Chemical compound OCCC1CC1 LUNMJRJMSXZSLC-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
ZJKVAVOAEMCJGI-UHFFFAOYSA-N 2-thiophen-3-yloxyacetic acid Chemical compound OC(=O)COC=1C=CSC=1 ZJKVAVOAEMCJGI-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
OGMHLZVDKIJTMN-UHFFFAOYSA-N 3-methylpentanoyl chloride Chemical compound CCC(C)CC(Cl)=O OGMHLZVDKIJTMN-UHFFFAOYSA-N 0.000 description 1
MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
240000004972 Bergenia crassifolia Species 0.000 description 1
235000014785 Bergenia crassifolia Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
241001416152 Bos frontalis Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
239000005770 Eugenol Substances 0.000 description 1
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239000005792 Geraniol Substances 0.000 description 1
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101001126084 Homo sapiens Piwi-like protein 2 Proteins 0.000 description 1
GFDFZTFQPIBNSQ-LDIYZUBKSA-N Homoormosanine Natural products N12[C@H]3[C@H](C[C@H]4[C@@H]5N(C[C@@]3([C@@H]3N(C1)CCCC3)C4)CCCC5)CCC2 GFDFZTFQPIBNSQ-LDIYZUBKSA-N 0.000 description 1
235000019501 Lemon oil Nutrition 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
102100029365 Piwi-like protein 2 Human genes 0.000 description 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
244000223014 Syzygium aromaticum Species 0.000 description 1
235000016639 Syzygium aromaticum Nutrition 0.000 description 1
101150052863 THY1 gene Proteins 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
241000396377 Tranes Species 0.000 description 1
101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
GYMWQLRSSDFGEQ-ADRAWKNSSA-N [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 GYMWQLRSSDFGEQ-ADRAWKNSSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
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UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
235000002783 ambrette Nutrition 0.000 description 1
244000096712 ambrette Species 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000010627 cedar oil Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000019219 chocolate Nutrition 0.000 description 1
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239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000009937 cyclo 3 Substances 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000001942 cyclopropanes Chemical class 0.000 description 1
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239000002270 dispersing agent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
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210000003608 fece Anatomy 0.000 description 1
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125000001153 fluoro group Chemical group F* 0.000 description 1
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239000007789 gas Substances 0.000 description 1
229940113087 geraniol Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
GFDFZTFQPIBNSQ-WSBLSWJJSA-N jamine Chemical compound C([C@H]([C@H]12)C3)CCN2CN2CCCC[C@@H]2[C@]21CN1CCCC[C@@H]1[C@H]3C2 GFDFZTFQPIBNSQ-WSBLSWJJSA-N 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000010501 lemon oil Substances 0.000 description 1
CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
239000010871 livestock manure Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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239000003607 modifier Substances 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
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230000007935 neutral effect Effects 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 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
239000012074 organic phase Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
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150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
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239000002243 precursor Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
239000001585 thymus vulgaris Substances 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 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
230000003245 working effect Effects 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
- 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
- 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Pyridine Compounds (AREA)
Pyrrole Compounds (AREA)
Cosmetics (AREA)

NL8204355A 1981-11-10 1982-11-10 Nieuwe cyclopropaanverbindingen, werkwijze voor hun bereiding, hun toepassing als reukstoffen en samenstellingen, die hen bevatten. NL8204355A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8121009		1981-11-10
FR8121009A FR2516076B1 (fr)	1981-11-10	1981-11-10	Nouveaux derives du cyclopropane, leur procede de preparation et leur application a la preparation de compositions parfumantes

Publications (1)

Publication Number	Publication Date
NL8204355A true NL8204355A (nl)	1983-06-01

Family

ID=9263855

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8204355A NL8204355A (nl)	1981-11-10	1982-11-10	Nieuwe cyclopropaanverbindingen, werkwijze voor hun bereiding, hun toepassing als reukstoffen en samenstellingen, die hen bevatten.

Country Status (8)

Country	Link
US (1)	US4521331A (ja)
JP (1)	JPS5890529A (ja)
CH (1)	CH653668A5 (ja)
DE (1)	DE3241586A1 (ja)
FR (1)	FR2516076B1 (ja)
GB (1)	GB2108962B (ja)
IT (1)	IT1186700B (ja)
NL (1)	NL8204355A (ja)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2516076B1 (fr) *	1981-11-10	1986-05-16	Roussel Uclaf	Nouveaux derives du cyclopropane, leur procede de preparation et leur application a la preparation de compositions parfumantes
EP1003469A2 (en) *	1996-02-21	2000-05-31	Givaudan-Roure (International) S.A.	Fragrance precursors
AU2935900A (en) *	1999-03-26	2000-10-16	Firmenich S.A.	Cyclic compounds and their use as precursors of fragrant alcohols
US20030089885A1 (en) *	2001-04-25	2003-05-15	Senomyx, Inc.	Use of low molecular weight acetal, alcohol, acylated alcohol and ester compounds to block or reduce odor of carboxylic acids
US6753303B2 (en) *	2001-12-06	2004-06-22	Hershey Entertainment & Resorts Company	Whipped cocoa bath
US20050119156A1 (en) *	2001-12-19	2005-06-02	Luca Turin	Aromachemicals
US20050096852A1 (en) *	2001-12-19	2005-05-05	Luca Turin	Method for increasing the stability and intensity of odorant molecules
WO2003053903A1 (en) *	2001-12-19	2003-07-03	Flexitral, Inc.	Improved citral derivatives
EP1705171A1 (en) *	2001-12-19	2006-09-27	Flexitral, Inc.	Improved aromachemicals
US7309795B2 (en) *	2001-12-19	2007-12-18	Luca Turin	Citral derivatives
US7342042B2 (en) *	2001-12-19	2008-03-11	Flexitral, Inc.	Lily of the valley aromachemicals
JP4212036B2 (ja) *	2003-06-19	2009-01-21	ローム株式会社	定電圧発生器
EP2132168A1 (en) *	2006-04-03	2009-12-16	Flexitral, Inc.	Aromachemicals comprising a nitrile group
IL187913A0 (en) *	2006-12-06	2008-12-29	Benjamin Bogomolny	Composition for improving plant growth and yield and method for using same
PT2493842T (pt) *	2009-10-30	2018-05-28	Nz Inst Plant & Food Res Ltd	Derivados de crisantemilo como atratores de cochonilha
US10407378B2 (en)	2014-04-21	2019-09-10	Takasago International Corporation	Compound, and flavor and/or fragrance composition containing said compound
JP6659440B2 (ja) *	2016-04-25	2020-03-04	国立研究開発法人農業・食品産業技術総合研究機構	クロテンコナカイガラムシの性誘引物質
JP6659439B2 (ja) *	2016-04-25	2020-03-04	国立研究開発法人農業・食品産業技術総合研究機構	フタスジコナカイガラムシの性誘引物質

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4258205A (en) *	1977-12-16	1981-03-24	Shell Oil Company	2,2-Dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives
GB2025963B (en) *	1978-07-19	1982-10-13	Shell Int Research	Cyclopropane derivative
US4298757A (en) *	1978-07-19	1981-11-03	Shell Oil Company	2-[2-(2,2-Dihalovinyl)-3,3-dimethylcyclopropyl ]vinyl alkanoates
GB2025962B (en) *	1978-07-19	1982-10-13	Shell Int Research	Cyclopropane derivatives
CA1150299A (en) *	1978-08-17	1983-07-19	Pieter A. Verbrugge	Intermediates in the preparation of cyclopropane-carboxylate esters and process for their manufacture
FR2516076B1 (fr) *	1981-11-10	1986-05-16	Roussel Uclaf	Nouveaux derives du cyclopropane, leur procede de preparation et leur application a la preparation de compositions parfumantes

1981
- 1981-11-10 FR FR8121009A patent/FR2516076B1/fr not_active Expired
1982
- 1982-11-02 US US06/438,486 patent/US4521331A/en not_active Expired - Fee Related
- 1982-11-09 CH CH6515/82A patent/CH653668A5/fr not_active IP Right Cessation
- 1982-11-09 IT IT49457/82A patent/IT1186700B/it active
- 1982-11-09 GB GB08231981A patent/GB2108962B/en not_active Expired
- 1982-11-10 NL NL8204355A patent/NL8204355A/nl not_active Application Discontinuation
- 1982-11-10 DE DE19823241586 patent/DE3241586A1/de not_active Withdrawn
- 1982-11-10 JP JP57196171A patent/JPS5890529A/ja active Pending

Also Published As

Publication number	Publication date
JPS5890529A (ja)	1983-05-30
GB2108962A (en)	1983-05-25
IT8249457A0 (it)	1982-11-09
CH653668A5 (fr)	1986-01-15
FR2516076A1 (fr)	1983-05-13
GB2108962B (en)	1986-04-23
IT1186700B (it)	1987-12-04
DE3241586A1 (de)	1983-05-19
US4521331A (en)	1985-06-04
FR2516076B1 (fr)	1986-05-16

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1990-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8204355A (nl)	1983-06-01	Nieuwe cyclopropaanverbindingen, werkwijze voor hun bereiding, hun toepassing als reukstoffen en samenstellingen, die hen bevatten.
JP3802346B2 (ja)	2006-07-26	ジャコウ香気を有するエステル及び香料でのその使用
US20040234568A1 (en)	2004-11-25	Cycloalkanecarboxylic acid derivatives as fragants with musk characteristics
EP0743297B1 (de)	2000-01-19	Neue Riechstoffe
US4456561A (en)	1984-06-26	Nitriles and use as perfume chemicals
DE60009394T2 (de)	2005-02-24	Cyclopentylalkylnitrile und die Verwendung von Cyclopentylalkyl-Derivaten als Duftstoffe
EP0137419B1 (de)	1987-08-12	Riechstoffkompositionen mit einem Gehalt an Benzyläthern
US3948814A (en)	1976-04-06	Acetaldehyde ethyl linalyl acetal perfume compositions
US4018838A (en)	1977-04-19	Process of preparing alkenes
Harris Jr	1972	. alpha.-and. beta.-(Trifluoromethylthio) acrylic acid derivatives
EP0278384B1 (de)	1993-09-29	Alkohole und Ether mit Cyclododecyl- und Cyclododecenylgruppen, deren Herstellung und Verwendung als Duftstoffe
EP0301375B1 (de)	1992-03-18	Bicyclische Aldehyde
EP0002510B1 (de)	1981-02-11	Cyclohexane, Verfahren zu deren Herstellung, deren Verwendung und diese enthaltende Kompositionen
JPH078834B2 (ja)	1995-02-01	置換されたビニル鎖により３位置が置換された新規なシクロプロパンカルボン酸
DE2812288C2 (ja)	1988-03-31
JPS5982345A (ja)	1984-05-12	アレン構造を有するシクロプロパンカルボン酸化合物、その製造方法及びそれを含有する寄生虫撲滅用組成物
US4132677A (en)	1979-01-02	Perfume compositions containing 2-(2-cyanoethylidene)-2-methyl-bicyclo(2.2.1)hept-5-enes
NL8200342A (nl)	1982-09-01	Nieuwe, op plaats 3 door een vinylketen gesubstitueerde, cyclopropaancarbonzuurverbindingen, hun bereiding, hun toepassing als reukmiddelen en de samenstellingen die zij bevatten.
US5011970A (en)	1991-04-30	Nitriles useful in perfume
EP1149820B1 (de)	2003-07-30	2-,5-,6-,7-,8-Substituierte Oct-2-en-4-one
DE2917450A1 (de)	1979-11-15	Neue alicyclische ketone, ihre verwendung und verfahren zu ihrer herstellung
US4609491A (en)	1986-09-02	Tri- and tetra-substituted cyclohexen-1-methyl acetates as odorants
US6284900B1 (en)	2001-09-04	Cis-isoambrettolide of high degree of isomer purity and use thereof
JPS6372639A (ja)	1988-04-02	２−三級ブチル−４−メチル−シクロヘキサノ−ル誘導体
DE2154244B2 (de)	1981-03-19	Cyclopentanone, ihre Herstellung und Verwendung als Riechstoffe