JPS61293391A - 補酵素ｑの製造法 - Google Patents
補酵素ｑの製造法Info
- Publication number
- JPS61293391A JPS61293391A JP13303185A JP13303185A JPS61293391A JP S61293391 A JPS61293391 A JP S61293391A JP 13303185 A JP13303185 A JP 13303185A JP 13303185 A JP13303185 A JP 13303185A JP S61293391 A JPS61293391 A JP S61293391A
- Authority
- JP
- Japan
- Prior art keywords
- coenzyme
- solvent
- dried
- microbial cells
- dimethyl sulfoxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000005515 coenzyme Substances 0.000 title abstract description 8
- 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 claims abstract description 35
- 235000017471 coenzyme Q10 Nutrition 0.000 claims abstract description 34
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 230000000813 microbial effect Effects 0.000 claims abstract description 8
- 238000000605 extraction Methods 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 15
- 238000004440 column chromatography Methods 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000005119 centrifugation Methods 0.000 abstract 1
- 239000012531 culture fluid Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 230000001580 bacterial effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DDEDPQYNISJXLF-XTMYEIJHSA-N [(z)-4-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-3-benzoylsulfanylpent-3-enyl] benzoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)OCC\C(SC(=O)C=1C=CC=CC=1)=C(/C)N(C=O)CC1=CN=C(C)N=C1N DDEDPQYNISJXLF-XTMYEIJHSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 210000004748 cultured cell Anatomy 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 241000223651 Aureobasidium Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000027721 electron transport chain Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000004059 quinone derivatives Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- SOECUQMRSRVZQQ-UHFFFAOYSA-N ubiquinone-1 Chemical compound COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O SOECUQMRSRVZQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13303185A JPS61293391A (ja) | 1985-06-20 | 1985-06-20 | 補酵素ｑの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13303185A JPS61293391A (ja) | 1985-06-20 | 1985-06-20 | 補酵素ｑの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61293391A true JPS61293391A (ja) | 1986-12-24 |
| JPS639838B2 JPS639838B2 (enrdf_load_stackoverflow) | 1988-03-02 |
Family
ID=15095186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13303185A Granted JPS61293391A (ja) | 1985-06-20 | 1985-06-20 | 補酵素ｑの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61293391A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004011660A1 (ja) * | 2002-07-25 | 2004-02-05 | Kyowa Hakko Kogyo Co., Ltd. | ユビキノン−１０含有溶液の製造方法 |
| WO2004051259A1 (ja) * | 2002-12-03 | 2004-06-17 | Shiseido Company, Ltd. | コエンザイムｑ−１０およびその２電子還元体の分析方法ならびに分析システム |
| WO2010006498A1 (zh) * | 2008-07-17 | 2010-01-21 | Ren Lei | 还原型辅酶q10的制备方法 |
-
1985
- 1985-06-20 JP JP13303185A patent/JPS61293391A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004011660A1 (ja) * | 2002-07-25 | 2004-02-05 | Kyowa Hakko Kogyo Co., Ltd. | ユビキノン−１０含有溶液の製造方法 |
| CN1308455C (zh) * | 2002-07-25 | 2007-04-04 | 协和发酵工业株式会社 | 含有辅酶q10的溶液的制备方法 |
| WO2004051259A1 (ja) * | 2002-12-03 | 2004-06-17 | Shiseido Company, Ltd. | コエンザイムｑ−１０およびその２電子還元体の分析方法ならびに分析システム |
| US7374901B2 (en) | 2002-12-03 | 2008-05-20 | Shiseido Company Ltd. | Method of analyzing coenzyme Q-10 and two-electron reduction product thereof and analysis system |
| WO2010006498A1 (zh) * | 2008-07-17 | 2010-01-21 | Ren Lei | 还原型辅酶q10的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS639838B2 (enrdf_load_stackoverflow) | 1988-03-02 |
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