CA2453158C - Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect - Google Patents
Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect Download PDFInfo
- Publication number
- CA2453158C CA2453158C CA2453158A CA2453158A CA2453158C CA 2453158 C CA2453158 C CA 2453158C CA 2453158 A CA2453158 A CA 2453158A CA 2453158 A CA2453158 A CA 2453158A CA 2453158 C CA2453158 C CA 2453158C
- Authority
- CA
- Canada
- Prior art keywords
- reduced coenzyme
- crystallization
- solvent
- coenzyme
- hydrocarbons
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002904 solvent Substances 0.000 title claims abstract description 108
- 238000000034 method Methods 0.000 title claims abstract description 49
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 title claims abstract description 43
- 230000000694 effects Effects 0.000 title description 15
- 238000002425 crystallisation Methods 0.000 claims abstract description 73
- 230000008025 crystallization Effects 0.000 claims abstract description 70
- -1 fatty acid esters Chemical class 0.000 claims abstract description 47
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 25
- 229930195729 fatty acid Natural products 0.000 claims abstract description 25
- 239000000194 fatty acid Substances 0.000 claims abstract description 25
- 150000002825 nitriles Chemical class 0.000 claims abstract description 23
- 150000002170 ethers Chemical class 0.000 claims abstract description 22
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims abstract description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 60
- 239000013078 crystal Substances 0.000 claims description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 54
- 238000006722 reduction reaction Methods 0.000 claims description 54
- 238000003756 stirring Methods 0.000 claims description 41
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 10
- 239000012298 atmosphere Substances 0.000 claims description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
- 150000008282 halocarbons Chemical class 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 6
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 claims description 6
- NPCOQXAVBJJZBQ-WJNLUYJISA-N ubiquinol-9 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-WJNLUYJISA-N 0.000 claims description 6
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 5
- PFIUSPPKANBDHQ-RJYQSXAYSA-N ubiquinol-7 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC PFIUSPPKANBDHQ-RJYQSXAYSA-N 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 2
- LOJUQFSPYHMHEO-SGHXUWJISA-N ubiquinol-8 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC LOJUQFSPYHMHEO-SGHXUWJISA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 17
- 238000007254 oxidation reaction Methods 0.000 abstract description 17
- 230000003647 oxidation Effects 0.000 abstract description 16
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 230000002194 synthesizing effect Effects 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 6
- 235000013305 food Nutrition 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 235000015097 nutrients Nutrition 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 235000015872 dietary supplement Nutrition 0.000 abstract description 2
- 235000013402 health food Nutrition 0.000 abstract description 2
- 230000000050 nutritive effect Effects 0.000 abstract description 2
- 230000003449 preventive effect Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000005515 coenzyme Substances 0.000 description 168
- 230000002829 reductive effect Effects 0.000 description 128
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 235000019441 ethanol Nutrition 0.000 description 37
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 34
- 125000004432 carbon atom Chemical group C* 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 230000009467 reduction Effects 0.000 description 28
- 229960005070 ascorbic acid Drugs 0.000 description 25
- 239000002002 slurry Substances 0.000 description 25
- 239000011668 ascorbic acid Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 239000003638 chemical reducing agent Substances 0.000 description 20
- 239000012071 phase Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 18
- 150000003839 salts Chemical group 0.000 description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 235000010323 ascorbic acid Nutrition 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 239000011261 inert gas Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
- 229910001882 dioxygen Inorganic materials 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 8
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 230000008030 elimination Effects 0.000 description 7
- 238000003379 elimination reaction Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 6
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
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- 239000002075 main ingredient Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 6
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 6
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
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- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 4
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
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- 230000007423 decrease Effects 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
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- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
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- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/46—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/814—Enzyme separation or purification
- Y10S435/816—Enzyme separation or purification by solubility
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001214471 | 2001-07-13 | ||
| JP2001-214471 | 2001-07-13 | ||
| JP2002-114854 | 2002-04-17 | ||
| JP2002114854 | 2002-04-17 | ||
| PCT/JP2002/007143 WO2003006408A1 (fr) | 2001-07-13 | 2002-07-15 | Procede de production de coenzyme q10 reduite a l'aide d'un solvant ayant un effet anti-oxydation puissant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2453158A1 CA2453158A1 (en) | 2003-01-23 |
| CA2453158C true CA2453158C (en) | 2011-05-24 |
Family
ID=26618740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2453158A Expired - Lifetime CA2453158C (en) | 2001-07-13 | 2002-07-15 | Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7145044B2 (en:Method) |
| EP (4) | EP2402303A3 (en:Method) |
| JP (1) | JP4057523B2 (en:Method) |
| KR (1) | KR100876509B1 (en:Method) |
| CN (3) | CN101906026A (en:Method) |
| AU (1) | AU2002318843B2 (en:Method) |
| CA (1) | CA2453158C (en:Method) |
| TW (1) | TWI310029B (en:Method) |
| WO (1) | WO2003006408A1 (en:Method) |
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| JP3822479B2 (ja) | 2001-10-10 | 2006-09-20 | 株式会社カネカ | 還元型補酵素ｑ水溶液の安定化組成 |
| TWI329510B (en) * | 2001-10-10 | 2010-09-01 | Kaneka Corp | Method of stabilizing reduced coenzyme q10 |
| TWI349039B (en) | 2001-12-27 | 2011-09-21 | Kaneka Corp | Processes for producing coenzyme q10 |
| AU2004278194B2 (en) * | 2003-09-10 | 2009-12-03 | Kaneka Corporation | Reduced coenzyme Q10 crystal excelling in stability and composition containing reduced coenzyme Q10 crystal |
| US7358402B2 (en) | 2003-09-10 | 2008-04-15 | Kaneka Corporation | Reduced coenzyme Q10 crystal with excellent stability and composition containing said reduced coenzyme Q10 crystal |
| US20060147542A1 (en) * | 2004-12-24 | 2006-07-06 | Tadao Ono | Solid preparation containing reduced coenzyme Q10 and method for producing the same |
| US8067217B2 (en) | 2004-12-28 | 2011-11-29 | Kaneka Corporation | Method for preserving reduced coenzyme Q10 |
| WO2006104153A1 (ja) * | 2005-03-29 | 2006-10-05 | Kaneka Corporation | 血液中の抗酸化活性を高める組成物 |
| JP4469772B2 (ja) * | 2005-09-15 | 2010-05-26 | 株式会社資生堂 | コエンザイムｑ１０高負荷細胞の作製方法、コエンザイムｑ１０高負荷細胞増殖添加剤及びコエンザイムｑ１０高負荷培地 |
| US8506956B2 (en) | 2005-10-31 | 2013-08-13 | Kaneka Corporation | Method for stabilizing reduced coenzyme Q10 |
| EP2025662A4 (en) * | 2006-04-28 | 2011-07-27 | Kaneka Corp | PROCESS FOR PURIFYING REDUCED COENZYME Q10 |
| US7829080B2 (en) | 2006-04-28 | 2010-11-09 | Kaneka Corporation | Stabilization method of reduced coenzyme Q10 |
| TW200826924A (en) | 2006-09-08 | 2008-07-01 | Kaneka Corp | Composition containing reduced coenzyme Q10 and lysolecithin |
| JP5558823B2 (ja) * | 2007-10-05 | 2014-07-23 | 株式会社カネカ | 還元型補酵素ｑ１０の製造方法 |
| WO2009057611A1 (ja) * | 2007-10-30 | 2009-05-07 | Kaneka Corporation | 含水有機溶媒を用いる還元型補酵素ｑ１０の製造方法 |
| EP2548456B1 (en) | 2008-03-20 | 2015-07-08 | Virun, Inc. | Emulsions including a PEG-derivative of tocopherol |
| CN102131407B (zh) * | 2008-06-23 | 2015-01-07 | 维尔恩公司 | 含有非极性化合物的组合物 |
| CN101514148B (zh) * | 2009-03-27 | 2015-05-13 | 玉溪健坤生物药业有限公司 | 一种还原型辅酶q10的制备方法 |
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-
2002
- 2002-07-12 TW TW091115489A patent/TWI310029B/zh not_active IP Right Cessation
- 2002-07-15 AU AU2002318843A patent/AU2002318843B2/en not_active Expired
- 2002-07-15 KR KR1020047000449A patent/KR100876509B1/ko not_active Expired - Lifetime
- 2002-07-15 CA CA2453158A patent/CA2453158C/en not_active Expired - Lifetime
- 2002-07-15 CN CN2010101807452A patent/CN101906026A/zh active Pending
- 2002-07-15 WO PCT/JP2002/007143 patent/WO2003006408A1/ja not_active Ceased
- 2002-07-15 EP EP11179276A patent/EP2402303A3/en not_active Ceased
- 2002-07-15 JP JP2003512182A patent/JP4057523B2/ja not_active Expired - Lifetime
- 2002-07-15 EP EP10159877A patent/EP2228360A1/en not_active Ceased
- 2002-07-15 CN CNA028141369A patent/CN1527807A/zh active Pending
- 2002-07-15 EP EP02746036A patent/EP1415969A4/en not_active Ceased
- 2002-07-15 US US10/483,604 patent/US7145044B2/en not_active Expired - Lifetime
- 2002-07-15 CN CN200910266328.7A patent/CN101774996B/zh not_active Expired - Lifetime
- 2002-07-15 EP EP17185148.8A patent/EP3321248A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2003006408A1 (ja) | 2004-10-28 |
| EP1415969A4 (en) | 2005-04-27 |
| WO2003006408A1 (fr) | 2003-01-23 |
| EP2402303A2 (en) | 2012-01-04 |
| CN1527807A (zh) | 2004-09-08 |
| TWI310029B (en:Method) | 2009-05-21 |
| CN101774996B (zh) | 2015-02-11 |
| AU2002318843B2 (en) | 2008-10-30 |
| US20040215040A1 (en) | 2004-10-28 |
| KR20040017293A (ko) | 2004-02-26 |
| EP3321248A2 (en) | 2018-05-16 |
| JP4057523B2 (ja) | 2008-03-05 |
| AU2002318843A2 (en) | 2003-01-29 |
| EP2402303A3 (en) | 2012-04-25 |
| EP3321248A3 (en) | 2018-06-06 |
| EP2228360A1 (en) | 2010-09-15 |
| EP1415969A1 (en) | 2004-05-06 |
| CN101774996A (zh) | 2010-07-14 |
| CA2453158A1 (en) | 2003-01-23 |
| KR100876509B1 (ko) | 2008-12-31 |
| US7145044B2 (en) | 2006-12-05 |
| CN101906026A (zh) | 2010-12-08 |
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