RU2286331C2 - Способ выделения стереоизомера (-)-ментола - Google Patents
Способ выделения стереоизомера (-)-ментола Download PDFInfo
- Publication number
- RU2286331C2 RU2286331C2 RU2003103292/04A RU2003103292A RU2286331C2 RU 2286331 C2 RU2286331 C2 RU 2286331C2 RU 2003103292/04 A RU2003103292/04 A RU 2003103292/04A RU 2003103292 A RU2003103292 A RU 2003103292A RU 2286331 C2 RU2286331 C2 RU 2286331C2
- Authority
- RU
- Russia
- Prior art keywords
- compound
- lipase
- formula
- stereoisomers
- enzyme
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 55
- 150000000083 (-)-menthol derivatives Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims abstract description 55
- 102000004190 Enzymes Human genes 0.000 claims abstract description 48
- 108090000790 Enzymes Proteins 0.000 claims abstract description 48
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 229960004873 levomenthol Drugs 0.000 claims abstract description 15
- 238000004821 distillation Methods 0.000 claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000005886 esterification reaction Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 108090001060 Lipase Proteins 0.000 claims description 34
- 102000004882 Lipase Human genes 0.000 claims description 34
- 239000004367 Lipase Substances 0.000 claims description 34
- 235000019421 lipase Nutrition 0.000 claims description 34
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 108090000371 Esterases Proteins 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 230000000707 stereoselective effect Effects 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- 241001661345 Moesziomyces antarcticus Species 0.000 claims description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 108010013563 Lipoprotein Lipase Proteins 0.000 claims description 7
- 102000043296 Lipoprotein lipases Human genes 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 240000006439 Aspergillus oryzae Species 0.000 claims description 5
- 235000002247 Aspergillus oryzae Nutrition 0.000 claims description 5
- 241000235403 Rhizomucor miehei Species 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 108091005804 Peptidases Proteins 0.000 claims description 4
- 239000004365 Protease Substances 0.000 claims description 4
- 101001003495 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 4
- 101001064559 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 4
- 241000589774 Pseudomonas sp. Species 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 229940116333 ethyl lactate Drugs 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- 230000006340 racemization Effects 0.000 claims description 4
- 241000589513 Burkholderia cepacia Species 0.000 claims description 3
- 235000019687 Lamb Nutrition 0.000 claims description 3
- -1 Novozyme 868 Proteins 0.000 claims description 3
- 108010073038 Penicillin Amidase Proteins 0.000 claims description 3
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 3
- 108010056079 Subtilisins Proteins 0.000 claims description 3
- 102000005158 Subtilisins Human genes 0.000 claims description 3
- 210000000496 pancreas Anatomy 0.000 claims description 3
- 230000000717 retained effect Effects 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 241001453380 Burkholderia Species 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 2
- 102000013392 Carboxylesterase Human genes 0.000 claims description 2
- 108010051152 Carboxylesterase Proteins 0.000 claims description 2
- 241000146387 Chromobacterium viscosum Species 0.000 claims description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 108010084311 Novozyme 435 Proteins 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 241000193390 Parageobacillus thermoglucosidasius Species 0.000 claims description 2
- 241000588264 Rhizopus javanicus Species 0.000 claims description 2
- 101000966371 Rhizopus niveus Lipase Proteins 0.000 claims description 2
- 241000179532 [Candida] cylindracea Species 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000010953 base metal Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 2
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 2
- 210000003918 fraction a Anatomy 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 239000003350 kerosene Substances 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 229940040461 lipase Drugs 0.000 claims 15
- 229940088598 enzyme Drugs 0.000 claims 10
- 125000001755 (-)-menthol group Chemical group 0.000 claims 1
- 241000193385 Geobacillus stearothermophilus Species 0.000 claims 1
- 241000498617 Mucor javanicus Species 0.000 claims 1
- 102000019280 Pancreatic lipases Human genes 0.000 claims 1
- 108050006759 Pancreatic lipases Proteins 0.000 claims 1
- 240000000064 Penicillium roqueforti Species 0.000 claims 1
- 235000002233 Penicillium roqueforti Nutrition 0.000 claims 1
- 240000005384 Rhizopus oryzae Species 0.000 claims 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 claims 1
- 241000698291 Rugosa Species 0.000 claims 1
- 241000235015 Yarrowia lipolytica Species 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 229940116369 pancreatic lipase Drugs 0.000 claims 1
- 238000002955 isolation Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 229940041616 menthol Drugs 0.000 description 23
- 230000008569 process Effects 0.000 description 20
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 7
- 239000005844 Thymol Substances 0.000 description 7
- 229960000790 thymol Drugs 0.000 description 7
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 108010093096 Immobilized Enzymes Proteins 0.000 description 4
- 241000235395 Mucor Species 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000016257 Mentha pulegium Nutrition 0.000 description 2
- 235000004357 Mentha x piperita Nutrition 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 2
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 2
- 235000001050 hortel pimenta Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 229940075966 (+)- menthol Drugs 0.000 description 1
- NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MKNXSXHFZBPBCK-UHFFFAOYSA-N 4-methyl-2-(5-methyl-2-propan-2-ylcyclohexyl)oxy-1-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(C)CC1OC1C(C(C)C)CCC(C)C1 MKNXSXHFZBPBCK-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 108091007474 BsteE Proteins 0.000 description 1
- 0 CC(CCC1*)CC1OC(*)=O Chemical compound CC(CCC1*)CC1OC(*)=O 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 241001479543 Mentha x piperita Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 101000968489 Rhizomucor miehei Lipase Proteins 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- XHXUANMFYXWVNG-WCQGTBRESA-N [(1s,2r,5s)-5-methyl-2-propan-2-ylcyclohexyl] acetate Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O XHXUANMFYXWVNG-WCQGTBRESA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(II) oxide Inorganic materials [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 239000008257 shaving cream Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA2000/3417 | 2000-07-07 | ||
| ZA200003417 | 2000-07-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003103292A RU2003103292A (ru) | 2004-08-20 |
| RU2286331C2 true RU2286331C2 (ru) | 2006-10-27 |
Family
ID=25588814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003103292/04A RU2286331C2 (ru) | 2000-07-07 | 2001-06-11 | Способ выделения стереоизомера (-)-ментола |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7026144B2 (enExample) |
| EP (1) | EP1301452A2 (enExample) |
| JP (1) | JP2004502744A (enExample) |
| CN (1) | CN1240646C (enExample) |
| AU (2) | AU7864001A (enExample) |
| BR (1) | BR0112501A (enExample) |
| CZ (1) | CZ2003285A3 (enExample) |
| MX (1) | MXPA02012645A (enExample) |
| RU (1) | RU2286331C2 (enExample) |
| SK (1) | SK1642003A3 (enExample) |
| WO (1) | WO2002004384A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10196848T1 (de) * | 2000-11-02 | 2003-12-11 | Csir Pretoria | Verfahren zur Darstellung von (-)-Menthol und ähnlichen Verbindungen |
| US7189760B2 (en) * | 2004-04-02 | 2007-03-13 | Millennium Specialty Chemicals | Physiological cooling compositions containing highly purified ethyl ester of N-[[5-methyl-2-(1-methylethyl) cyclohexyl] carbonyl]glycine |
| KR100846674B1 (ko) | 2006-03-10 | 2008-07-16 | 엔자이텍 주식회사 | 효소적 방법에 의한 광학활성 트랜스 알코올 화합물 및 그의 에스테르 화합물 제조방법 |
| JP5603884B2 (ja) | 2009-02-17 | 2014-10-08 | 長岡実業株式会社 | 天然ｌ−メントールを生成するための方法及び装置 |
| CN104177233B (zh) * | 2014-09-10 | 2015-10-28 | 湖南湘易康制药有限公司 | 一种麝香草酚的合成方法 |
| CN104311392A (zh) * | 2014-10-12 | 2015-01-28 | 王同俊 | R-1-(3,4-二甲基苯基)乙醇及其酯的合成 |
| CN104311393A (zh) * | 2014-10-12 | 2015-01-28 | 王同俊 | 一种r-1-(3-氯苯基)乙醇及其酯的制备方法 |
| CN106397225A (zh) * | 2016-09-04 | 2017-02-15 | 王际菊 | 一种手性化合物的制备方法 |
| CN106380408A (zh) * | 2016-09-04 | 2017-02-08 | 王际菊 | 一种光学纯手性胺的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE568671C (de) | 1927-02-16 | 1933-01-24 | Rheinische Kampfer Fabrik G M | Verfahren zur Darstellung von inaktivem Menthol |
| DE538376C (de) | 1930-12-11 | 1931-11-14 | Oscar Hinsberg Dr | Verfahren zur Kernalkylierung von Phenolen und Phenolaethern sowie deren Kern-Substitutionsprodukten |
| JP3289058B2 (ja) * | 1992-09-11 | 2002-06-04 | 工業技術院長 | 酵素を用いたエステル製造方法 |
| DE60101509T2 (de) * | 2000-06-19 | 2004-10-14 | Loders Croklaan B.V. | Cla-ester |
-
2001
- 2001-06-11 WO PCT/IB2001/001008 patent/WO2002004384A2/en not_active Ceased
- 2001-06-11 AU AU7864001A patent/AU7864001A/xx active Pending
- 2001-06-11 US US10/312,996 patent/US7026144B2/en not_active Expired - Fee Related
- 2001-06-11 CZ CZ2003285A patent/CZ2003285A3/cs unknown
- 2001-06-11 EP EP01956722A patent/EP1301452A2/en not_active Withdrawn
- 2001-06-11 CN CNB018124291A patent/CN1240646C/zh not_active Expired - Fee Related
- 2001-06-11 BR BR0112501-0A patent/BR0112501A/pt not_active Application Discontinuation
- 2001-06-11 RU RU2003103292/04A patent/RU2286331C2/ru not_active IP Right Cessation
- 2001-06-11 AU AU2001278640A patent/AU2001278640B2/en not_active Ceased
- 2001-06-11 SK SK164-2003A patent/SK1642003A3/sk unknown
- 2001-06-11 JP JP2002509053A patent/JP2004502744A/ja active Pending
- 2001-06-11 MX MXPA02012645A patent/MXPA02012645A/es unknown
Non-Patent Citations (1)
| Title |
|---|
| E.CERMA et al. The role of the reaction medium in lipase-catalysed esterifications and transesterifications, CHEMISTRY AND PHYSICS OF LIPIDS, 1998, 93/1-2, p.157-168. * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7864001A (en) | 2002-01-21 |
| JP2004502744A (ja) | 2004-01-29 |
| WO2002004384A3 (en) | 2002-06-20 |
| CN1240646C (zh) | 2006-02-08 |
| BR0112501A (pt) | 2003-07-29 |
| CN1452603A (zh) | 2003-10-29 |
| AU2001278640B2 (en) | 2006-04-13 |
| WO2002004384A2 (en) | 2002-01-17 |
| SK1642003A3 (en) | 2003-08-05 |
| EP1301452A2 (en) | 2003-04-16 |
| US7026144B2 (en) | 2006-04-11 |
| MXPA02012645A (es) | 2004-09-10 |
| CZ2003285A3 (cs) | 2003-10-15 |
| US20030153031A1 (en) | 2003-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4963492A (en) | Method for the enzymatic racemate resolution of racemic alcohols with/in vinyl esters by transesterification | |
| JP3759621B2 (ja) | アスコルビン酸、２―ケト―ｌ―グロン酸及び２―ケト―ｌ―グロン酸のエステルの製造のための酵素的方法 | |
| RU2286331C2 (ru) | Способ выделения стереоизомера (-)-ментола | |
| US8466297B2 (en) | Manufacturing process for (S)-Pregabalin | |
| AU2001278640A1 (en) | Process for preparing (-)menthol and similar compounds | |
| KR100657212B1 (ko) | 라세믹 에스테르로부터 광학활성 에스테르 유도체와 이의 산의 제조 방법 | |
| EP0494203B1 (en) | Synthesis of aryl alkanediols having high optical purity | |
| RU2003103292A (ru) | Способ получения (-)-ментола и аналогичных соединений | |
| WO1996040975A1 (en) | Optical resolution of alkyl chroman-2-carboxylates | |
| ZA200300125B (en) | Process for preparing (-)menthol and similar compounds. | |
| Boaz | Enzymatic desymmetrization of cis-1, 3-cyclohexanedicarboxylic acid diesters | |
| JP4319260B2 (ja) | エステラーゼ遺伝子及びその利用 | |
| JP4843813B2 (ja) | 酵素を用いるＲ−体又はＳ−体のα−置換ヘテロサイクリックカルボン酸及びこれと反対鏡像の鏡像異性体のα−置換ヘテロサイクリックカルボン酸エステルの調製方法 | |
| JP4843812B2 (ja) | 酵素を使用するラセミα−置換ヘテロ環式カルボン酸の光学分割方法 | |
| US20040058422A1 (en) | Process for preparing (-)- menthol and similar compounds | |
| JPH09501834A (ja) | ジケテンを用いてのアルコールのリパーゼ触媒作用下でのアシル化 | |
| CN1644012A (zh) | 一株沙雷氏杆菌及其在制备地尔硫卓手性前体中的应用 | |
| EP0783039B1 (en) | Process for producing optically active 2-alkoxycyclohexanol derivatives | |
| JP2005117905A (ja) | 光学活性１−ベンジル−３−ピロリジノールの製造方法 | |
| EP1349950B1 (en) | A process for the preparation of 1-(3-trifluoromethylphenyl)-propan-2-ol enantiomers | |
| JPH1175889A (ja) | 光学活性α−トリフルオロメチル乳酸及びその対掌体エステルの製造方法及び精製方法 | |
| JPH08113550A (ja) | 光学活性３−ヒドロキシヘキサン酸類の製造方法 | |
| WO1984004543A1 (fr) | Procede de preparation de composes d'alcool benzylique optiquement actifs | |
| CN117511909A (zh) | 酯水解酶及其用途、维生素a棕榈酸酯的制备方法 | |
| JPH06319572A (ja) | ハロゲン化化合物の製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110612 |