RU2384557C2 - Новые производные триметилциклододекатриена, их применение и содержащие их парфюмерные продукты - Google Patents
Новые производные триметилциклододекатриена, их применение и содержащие их парфюмерные продукты Download PDFInfo
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- RU2384557C2 RU2384557C2 RU2007131287/04A RU2007131287A RU2384557C2 RU 2384557 C2 RU2384557 C2 RU 2384557C2 RU 2007131287/04 A RU2007131287/04 A RU 2007131287/04A RU 2007131287 A RU2007131287 A RU 2007131287A RU 2384557 C2 RU2384557 C2 RU 2384557C2
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- HKFWOZCGNIQGPI-PEJKQWNRSA-N (1Z,3Z,5Z)-1,2,3-trimethylcyclododeca-1,3,5-triene Chemical class C\C1=C(/C)\C(\C)=C/C=C\CCCCCC1 HKFWOZCGNIQGPI-PEJKQWNRSA-N 0.000 title 1
- 239000012437 perfumed product Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000002304 perfume Substances 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 239000000344 soap Substances 0.000 claims description 10
- 239000006071 cream Substances 0.000 claims description 9
- 150000002923 oximes Chemical class 0.000 claims description 9
- 239000006210 lotion Substances 0.000 claims description 8
- 239000012876 carrier material Substances 0.000 claims description 7
- 239000003599 detergent Substances 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 239000002453 shampoo Substances 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 5
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 5
- 230000001166 anti-perspirative effect Effects 0.000 claims description 4
- 239000003213 antiperspirant Substances 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 239000002781 deodorant agent Substances 0.000 claims description 4
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 4
- 239000002324 mouth wash Substances 0.000 claims description 4
- 239000000606 toothpaste Substances 0.000 claims description 4
- DRDYICOUDVAVGE-UHFFFAOYSA-N 1,5,10-trimethylcyclododeca-1,5,9-triene Chemical class CC1=CCCC=C(C)CCC(C)=CCC1 DRDYICOUDVAVGE-UHFFFAOYSA-N 0.000 claims description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 3
- 229920002774 Maltodextrin Polymers 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000002386 air freshener Substances 0.000 claims description 3
- 229940097362 cyclodextrins Drugs 0.000 claims description 3
- 239000003925 fat Substances 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- 229940051866 mouthwash Drugs 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000008257 shaving cream Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 229940034610 toothpaste Drugs 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 230000000873 masking effect Effects 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 5
- 239000003845 household chemical Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- -1 softeners Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- ZJASJPPUYJCUOK-UHFFFAOYSA-N 1-methoxy-2,3,4-trimethylcyclododeca-1,3-diene Chemical class COC1=C(C)C(C)=C(C)CCCCCCCC1 ZJASJPPUYJCUOK-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000003205 fragrance Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000000796 flavoring agent Substances 0.000 description 10
- 235000019634 flavors Nutrition 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 235000019645 odor Nutrition 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- GMOBHFXMODPGGZ-UHFFFAOYSA-N 2,3,4-trimethylcyclododeca-2,4,6-trien-1-one Chemical class CC1=CC=CCCCCCC(=O)C(C)=C1C GMOBHFXMODPGGZ-UHFFFAOYSA-N 0.000 description 6
- RMFIUAUMANXFMU-UHFFFAOYSA-N 5-chloro-2,3,4-trimethyl-1-nitrosocyclododeca-1,3-diene Chemical class CC1=C(C)C(C)=C(N=O)CCCCCCCC1Cl RMFIUAUMANXFMU-UHFFFAOYSA-N 0.000 description 6
- ZTCRFVAZUMZFAT-UHFFFAOYSA-N N-(2,3,4-trimethylcyclododeca-2,4,6-trien-1-ylidene)hydroxylamine Chemical class CC1=CC=CCCCCCC(=NO)C(C)=C1C ZTCRFVAZUMZFAT-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- OMQDQMRBFFMWTK-UHFFFAOYSA-N 1-methoxy-1,2,2-trimethylcyclododecane Chemical compound COC1(C)CCCCCCCCCCC1(C)C OMQDQMRBFFMWTK-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- HPTIDIPGIUCQFC-UHFFFAOYSA-N methoxymethoxycyclododecane Chemical compound COCOC1CCCCCCCCCCC1 HPTIDIPGIUCQFC-UHFFFAOYSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- DRDYICOUDVAVGE-MSKXPCFJSA-N (1z,5z,9z)-1,5,10-trimethylcyclododeca-1,5,9-triene Chemical compound C\C1=C\CC\C=C(C)/CC\C(C)=C/CC1 DRDYICOUDVAVGE-MSKXPCFJSA-N 0.000 description 4
- HKFWOZCGNIQGPI-UHFFFAOYSA-N 1,2,3-trimethylcyclododeca-1,3,5-triene Chemical class CC1=C(C)C(C)=CC=CCCCCCC1 HKFWOZCGNIQGPI-UHFFFAOYSA-N 0.000 description 4
- XOTMHDVYZZBKEJ-UHFFFAOYSA-N 1,5,9-trimethylcyclododeca-1,5,9-triene Chemical compound CC1=CCCC(C)=CCCC(C)=CCC1 XOTMHDVYZZBKEJ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- VQNUNMBDOKEZHS-UHFFFAOYSA-N ethoxymethoxycyclododecane Chemical compound CCOCOC1CCCCCCCCCCC1 VQNUNMBDOKEZHS-UHFFFAOYSA-N 0.000 description 4
- 150000002678 macrocyclic compounds Chemical class 0.000 description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 3
- IMVAJUFXBXSPRI-UHFFFAOYSA-N 1-ethoxy-2,3,4-trimethylcyclododeca-1,3-diene Chemical class CCOC1=C(C)C(C)=C(C)CCCCCCCC1 IMVAJUFXBXSPRI-UHFFFAOYSA-N 0.000 description 3
- 241000723346 Cinnamomum camphora Species 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 244000284012 Vetiveria zizanioides Species 0.000 description 3
- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 3
- 229960000846 camphor Drugs 0.000 description 3
- 229930008380 camphor Natural products 0.000 description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
- 229940008406 diethyl sulfate Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HRGPYCVTDOECMG-RHBQXOTJSA-N methyl cedryl ether Chemical compound C1[C@@]23[C@H](C)CC[C@H]2C(C)(C)[C@]1([H])[C@@](OC)(C)CC3 HRGPYCVTDOECMG-RHBQXOTJSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 2
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 2
- UXKLQDCALAWFIU-VKNDCNMPSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-tetradecoxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@H](O)[C@H](C(O2)(C(O)=O)C(O)(C(O1)C(O)=O)C(O)=O)OCCCCCCCCCCCCCC)C1=CC=CC=C1 UXKLQDCALAWFIU-VKNDCNMPSA-N 0.000 description 2
- VGNCBRNRHXEODV-XXVHXNRLSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-dodecoxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@H](O)[C@H](C(O2)(C(O)=O)C(O)(C(O1)C(O)=O)C(O)=O)OCCCCCCCCCCCC)C1=CC=CC=C1 VGNCBRNRHXEODV-XXVHXNRLSA-N 0.000 description 2
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 2
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 description 2
- DMXNJGKHNRHRFW-UHFFFAOYSA-N 2,3,4-trimethylcyclododeca-2,4-dien-1-one Chemical class CC1=CCCCCCCCC(=O)C(C)=C1C DMXNJGKHNRHRFW-UHFFFAOYSA-N 0.000 description 2
- MWDVCHRYCKXEBY-LBPRGKRZSA-N 3-chloro-n-[2-oxo-2-[[(1s)-1-phenylethyl]amino]ethyl]benzamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)CNC(=O)C1=CC=CC(Cl)=C1 MWDVCHRYCKXEBY-LBPRGKRZSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- CVRLKGSOROKIIO-UHFFFAOYSA-N 5,8,12-trimethylcyclododeca-4,8-dien-1-one Chemical compound CC1CCC=C(C)CCC(C)=CCCC1=O CVRLKGSOROKIIO-UHFFFAOYSA-N 0.000 description 2
- LDIOUQIXNSSOGU-UHFFFAOYSA-N 8-(3-pentylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidine Chemical compound CC1=NN2C(NC(CC)CC)=C3CCCC3=NC2=C1C1=CC=C(OC)C=C1Cl LDIOUQIXNSSOGU-UHFFFAOYSA-N 0.000 description 2
- YPZUZOLGGMJZJO-UHFFFAOYSA-N Ambronide Chemical compound C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- 241000402754 Erythranthe moschata Species 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
- KVWWIYGFBYDJQC-GHMZBOCLSA-N Methyl dihydrojasmonate Chemical compound CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-GHMZBOCLSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
- 150000001299 aldehydes Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- MIZGSAALSYARKU-UHFFFAOYSA-N cashmeran Chemical compound CC1(C)C(C)C(C)(C)C2=C1C(=O)CCC2 MIZGSAALSYARKU-UHFFFAOYSA-N 0.000 description 2
- HRGPYCVTDOECMG-UHFFFAOYSA-N cedrol methyl ether Chemical compound COC1(C)CCC2(C(CC3)C)C3C(C)(C)C1C2 HRGPYCVTDOECMG-UHFFFAOYSA-N 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 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
- 150000002431 hydrogen Chemical class 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HBEDNENASUYMPO-LJQANCHMSA-N n-hydroxy-4-[[(2r)-3-oxo-2-(thiophen-2-ylmethyl)-2,4-dihydroquinoxalin-1-yl]methyl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1CN1C2=CC=CC=C2NC(=O)[C@H]1CC1=CC=CS1 HBEDNENASUYMPO-LJQANCHMSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
- 239000001304 (2R)-2,6-dimethylhept-5-enal Substances 0.000 description 1
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- VJCOQIJZYGQPKM-FNORWQNLSA-N (3e)-undeca-1,3-dien-5-yne Chemical compound CCCCCC#C\C=C\C=C VJCOQIJZYGQPKM-FNORWQNLSA-N 0.000 description 1
- 229940098795 (3z)- 3-hexenyl acetate Drugs 0.000 description 1
- PAZWFUGWOAQBJJ-SWZPTJTJSA-N (4e,8e)-4,8,12-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene Chemical compound C1C\C(C)=C\CCC(/C)=C/CCC2(C)OC21 PAZWFUGWOAQBJJ-SWZPTJTJSA-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
- YKNBKTFSULDTKG-UHFFFAOYSA-N 1,2,3-trimethylcyclododeca-1,3-diene Chemical class CC1=C(C)C(C)=CCCCCCCCC1 YKNBKTFSULDTKG-UHFFFAOYSA-N 0.000 description 1
- FVUGZKDGWGKCFE-UHFFFAOYSA-N 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCCC2=C1CC(C(C)=O)(C)C(C)C2 FVUGZKDGWGKCFE-UHFFFAOYSA-N 0.000 description 1
- 239000001875 1-phenylethyl acetate Substances 0.000 description 1
- JWWNCSGMCRFKLK-UHFFFAOYSA-N 2,3,4-trimethylcyclododeca-1,3-dien-1-ol Chemical class CC1=C(C)C(C)=C(O)CCCCCCCC1 JWWNCSGMCRFKLK-UHFFFAOYSA-N 0.000 description 1
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- QPNXWGRYYRSVET-UHFFFAOYSA-N 3,7,11-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene Chemical compound CC1CC=CC(C)CC=CC(C)CC2OC21 QPNXWGRYYRSVET-UHFFFAOYSA-N 0.000 description 1
- JRJBVWJSTHECJK-PKNBQFBNSA-N 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Chemical compound CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-PKNBQFBNSA-N 0.000 description 1
- HTLBMZKXJYNJSK-UHFFFAOYSA-N 3-naphthalen-2-yl-1,2-oxazol-5-amine Chemical compound O1C(N)=CC(C=2C=C3C=CC=CC3=CC=2)=N1 HTLBMZKXJYNJSK-UHFFFAOYSA-N 0.000 description 1
- RWVATVBAGFDQQL-UHFFFAOYSA-N 4,8,12-trimethylcyclododeca-4,8-dien-1-one Chemical compound CC1CCC=C(C)CCC=C(C)CCC1=O RWVATVBAGFDQQL-UHFFFAOYSA-N 0.000 description 1
- INIOTLARNNSXAE-UHFFFAOYSA-N 4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1h-azulen-6-ol Chemical compound CC1CC(O)C=C(C)C2CC(=C(C)C)CC12 INIOTLARNNSXAE-UHFFFAOYSA-N 0.000 description 1
- XDCOYBQVEVSNNB-UHFFFAOYSA-N 4-[(7-naphthalen-2-yl-1-benzothiophen-2-yl)methylamino]butanoic acid Chemical compound OC(=O)CCCNCc1cc2cccc(-c3ccc4ccccc4c3)c2s1 XDCOYBQVEVSNNB-UHFFFAOYSA-N 0.000 description 1
- YVSNOTITPICPTB-UHFFFAOYSA-N 4-methyl-2-(2-methylpropyl)oxan-4-ol Chemical compound CC(C)CC1CC(C)(O)CCO1 YVSNOTITPICPTB-UHFFFAOYSA-N 0.000 description 1
- DASQRZJTRKBKPP-UHFFFAOYSA-N 5-butan-2-yl-2-(2,4-dimethylcyclohex-3-en-1-yl)-5-methyl-1,3-dioxane Chemical compound O1CC(C(C)CC)(C)COC1C1C(C)C=C(C)CC1 DASQRZJTRKBKPP-UHFFFAOYSA-N 0.000 description 1
- VDUIVSUSFAZIRM-UHFFFAOYSA-N 5h-1,4-dioxepin-3-one Chemical compound O=C1COC=CCO1 VDUIVSUSFAZIRM-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BROPQIFJUJTNPJ-JAMMHHFISA-N CCC(C(C)C)[C@H](C)N Chemical compound CCC(C(C)C)[C@H](C)N BROPQIFJUJTNPJ-JAMMHHFISA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 240000002943 Elettaria cardamomum Species 0.000 description 1
- 241000234269 Liliales Species 0.000 description 1
- 240000002262 Litsea cubeba Species 0.000 description 1
- 235000012854 Litsea cubeba Nutrition 0.000 description 1
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
- TZCCKCLHNUSAMQ-DUGSHLAESA-N NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N Chemical compound NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N TZCCKCLHNUSAMQ-DUGSHLAESA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 235000005300 cardamomo Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- NPFVOOAXDOBMCE-PLNGDYQASA-N cis-3-Hexenyl acetate Natural products CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
- RRGOKSYVAZDNKR-ARJAWSKDSA-M cis-3-hexenylacetate Chemical compound CC\C=C/CCCC([O-])=O RRGOKSYVAZDNKR-ARJAWSKDSA-M 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IUSBVFZKQJGVEP-SNAWJCMRSA-N isoeugenol acetate Chemical compound COC1=CC(\C=C\C)=CC=C1OC(C)=O IUSBVFZKQJGVEP-SNAWJCMRSA-N 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 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
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 239000010502 orange oil Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a nine to twelve-membered rings, e.g. cyclododecanols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0500550A FR2880883B1 (fr) | 2005-01-19 | 2005-01-19 | Nouveaux derives de trimethylcyclododecatriene, leur utilisation et produits parfumes les contenant |
| FR0500550 | 2005-01-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007131287A RU2007131287A (ru) | 2009-02-27 |
| RU2384557C2 true RU2384557C2 (ru) | 2010-03-20 |
Family
ID=34953253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007131287/04A RU2384557C2 (ru) | 2005-01-19 | 2006-01-13 | Новые производные триметилциклододекатриена, их применение и содержащие их парфюмерные продукты |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7737107B2 (https=) |
| EP (1) | EP1838653B1 (https=) |
| JP (1) | JP4956441B2 (https=) |
| CN (1) | CN101119958B (https=) |
| AT (1) | ATE476407T1 (https=) |
| BR (1) | BRPI0606673B1 (https=) |
| CY (1) | CY1110834T1 (https=) |
| DE (1) | DE602006015905D1 (https=) |
| DK (1) | DK1838653T3 (https=) |
| ES (1) | ES2348805T3 (https=) |
| FR (1) | FR2880883B1 (https=) |
| MX (1) | MX2007008788A (https=) |
| PL (1) | PL1838653T3 (https=) |
| RU (1) | RU2384557C2 (https=) |
| WO (1) | WO2006077306A1 (https=) |
| ZA (1) | ZA200706903B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2669029C1 (ru) * | 2014-11-10 | 2018-10-05 | Живодан Са | Усовершенствование органических соединений или усовершенствование, относящееся к органическим соединениям |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8722342B2 (en) | 2008-07-04 | 2014-05-13 | Sekisui Medical Co., Ltd. | Method for enhancing sensitivity or method for avoiding influence of hemoglobin in immunological measurement |
| US9217122B2 (en) * | 2011-06-22 | 2015-12-22 | Firmenich Sa | Cyclododecadienone derivatives as perfuming ingredients |
| EP3233034B1 (en) * | 2014-12-18 | 2019-02-27 | Firmenich SA | Macrocyclic ketone as malodor counteracting ingredient |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1528158A (fr) * | 1966-05-20 | 1968-06-07 | Int Flavors & Fragrances Inc | Nouveaux produits et procédés |
| US3723478A (en) * | 1965-05-11 | 1973-03-27 | Firmenich & Cie | Monoepoxidized products of dodecatriene |
| NL8700469A (nl) * | 1987-02-25 | 1988-09-16 | Naarden International Nv | Alkoholen, afgeleid van trimethyl-1,5,9-cyclodecatrieen, alsmede parfumcomposities en geparfumeerde produkten die een of meer van deze alkoholen als parfumgrondstof bevatten. |
| SU1657483A1 (ru) * | 1989-01-30 | 1991-06-23 | Институт элементоорганических соединений им.А.Н.Несмеянова | Способ получени циклододеканола |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845078A (en) * | 1966-05-20 | 1974-10-29 | Int Flavors & Fragrances Inc | 1,5,9-trimethylcyclododecatriene derivatives |
| ES340761A1 (es) * | 1966-05-20 | 1968-09-16 | Int Flavors & Fragrances Inc | Un metodo de preparacion de compuestos aromaticos. |
| US3714255A (en) * | 1971-08-26 | 1973-01-30 | Cities Service Co | Addition products of nitrosyl halides and cyclic unsaturated hydrocarbons |
| CH635810A5 (fr) * | 1978-12-21 | 1983-04-29 | Firmenich & Cie | Composes alicycliques insatures, procede pour leur preparation et leur utilisation. |
-
2005
- 2005-01-19 FR FR0500550A patent/FR2880883B1/fr not_active Expired - Lifetime
-
2006
- 2006-01-13 AT AT06709088T patent/ATE476407T1/de active
- 2006-01-13 ES ES06709088T patent/ES2348805T3/es not_active Expired - Lifetime
- 2006-01-13 RU RU2007131287/04A patent/RU2384557C2/ru active
- 2006-01-13 EP EP06709088A patent/EP1838653B1/fr not_active Expired - Lifetime
- 2006-01-13 BR BRPI0606673-9A patent/BRPI0606673B1/pt active IP Right Grant
- 2006-01-13 US US11/795,382 patent/US7737107B2/en not_active Expired - Lifetime
- 2006-01-13 MX MX2007008788A patent/MX2007008788A/es active IP Right Grant
- 2006-01-13 DE DE602006015905T patent/DE602006015905D1/de not_active Expired - Lifetime
- 2006-01-13 DK DK06709088.6T patent/DK1838653T3/da active
- 2006-01-13 CN CN2006800051609A patent/CN101119958B/zh not_active Expired - Lifetime
- 2006-01-13 WO PCT/FR2006/000081 patent/WO2006077306A1/fr not_active Ceased
- 2006-01-13 JP JP2007551699A patent/JP4956441B2/ja not_active Expired - Lifetime
- 2006-01-13 PL PL06709088T patent/PL1838653T3/pl unknown
-
2007
- 2007-08-17 ZA ZA2007/06903A patent/ZA200706903B/en unknown
-
2010
- 2010-10-18 CY CY20101100926T patent/CY1110834T1/el unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3723478A (en) * | 1965-05-11 | 1973-03-27 | Firmenich & Cie | Monoepoxidized products of dodecatriene |
| FR1528158A (fr) * | 1966-05-20 | 1968-06-07 | Int Flavors & Fragrances Inc | Nouveaux produits et procédés |
| NL8700469A (nl) * | 1987-02-25 | 1988-09-16 | Naarden International Nv | Alkoholen, afgeleid van trimethyl-1,5,9-cyclodecatrieen, alsmede parfumcomposities en geparfumeerde produkten die een of meer van deze alkoholen als parfumgrondstof bevatten. |
| SU1657483A1 (ru) * | 1989-01-30 | 1991-06-23 | Институт элементоорганических соединений им.А.Н.Несмеянова | Способ получени циклододеканола |
Non-Patent Citations (1)
| Title |
|---|
| CAS on STN, реферат №128: 3476: KUNITSKII A.A. ET AL. Synthesis of unsaturated alicyclic С8 and С12 1,2-diols from cycloolefin monoepoxides. Neftekhimiya, 1997, 37(3), с.259-265. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2669029C1 (ru) * | 2014-11-10 | 2018-10-05 | Живодан Са | Усовершенствование органических соединений или усовершенствование, относящееся к органическим соединениям |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006077306A1 (fr) | 2006-07-27 |
| CN101119958B (zh) | 2011-09-21 |
| EP1838653A1 (fr) | 2007-10-03 |
| CY1110834T1 (el) | 2015-06-10 |
| PL1838653T3 (pl) | 2011-01-31 |
| US7737107B2 (en) | 2010-06-15 |
| HK1109766A1 (zh) | 2008-06-20 |
| US20080139446A1 (en) | 2008-06-12 |
| MX2007008788A (es) | 2007-09-11 |
| EP1838653B1 (fr) | 2010-08-04 |
| ES2348805T3 (es) | 2010-12-14 |
| ATE476407T1 (de) | 2010-08-15 |
| CN101119958A (zh) | 2008-02-06 |
| BRPI0606673B1 (pt) | 2018-02-06 |
| DK1838653T3 (da) | 2010-11-29 |
| BRPI0606673A2 (pt) | 2016-09-27 |
| JP4956441B2 (ja) | 2012-06-20 |
| DE602006015905D1 (de) | 2010-09-16 |
| FR2880883A1 (fr) | 2006-07-21 |
| JP2008527024A (ja) | 2008-07-24 |
| ZA200706903B (en) | 2008-12-31 |
| FR2880883B1 (fr) | 2009-01-09 |
| RU2007131287A (ru) | 2009-02-27 |
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