CN110041184A - 一种维生素甲萘醌-7的提纯方法 - Google Patents
一种维生素甲萘醌-7的提纯方法 Download PDFInfo
- Publication number
- CN110041184A CN110041184A CN201910462407.9A CN201910462407A CN110041184A CN 110041184 A CN110041184 A CN 110041184A CN 201910462407 A CN201910462407 A CN 201910462407A CN 110041184 A CN110041184 A CN 110041184A
- Authority
- CN
- China
- Prior art keywords
- vitamin
- menaquinone
- purification
- organic solvent
- methanol
- 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
- PFRQBZFETXBLTP-UHFFFAOYSA-N Vitamin K2 Natural products C1=CC=C2C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C(=O)C2=C1 PFRQBZFETXBLTP-UHFFFAOYSA-N 0.000 title claims abstract description 86
- RAKQPZMEYJZGPI-LJWNYQGCSA-N menaquinone-7 Chemical compound C1=CC=C2C(=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)/CCC=C(C)C)=C(C)C(=O)C2=C1 RAKQPZMEYJZGPI-LJWNYQGCSA-N 0.000 title claims abstract description 86
- 235000009464 menaquinone-7 Nutrition 0.000 title claims abstract description 86
- 239000011700 menaquinone-7 Substances 0.000 title claims abstract description 86
- 229940088594 vitamin Drugs 0.000 title claims abstract description 44
- 229930003231 vitamin Natural products 0.000 title claims abstract description 44
- 235000013343 vitamin Nutrition 0.000 title claims abstract description 44
- 239000011782 vitamin Substances 0.000 title claims abstract description 44
- 150000003722 vitamin derivatives Chemical class 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000000746 purification Methods 0.000 title claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 239000011347 resin Substances 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 18
- 238000012856 packing Methods 0.000 claims abstract description 18
- 239000000945 filler Substances 0.000 claims abstract description 12
- 241000894006 Bacteria Species 0.000 claims abstract description 11
- 238000002425 crystallisation Methods 0.000 claims abstract description 11
- 230000008025 crystallization Effects 0.000 claims abstract description 11
- 238000001179 sorption measurement Methods 0.000 claims abstract description 10
- 238000005189 flocculation Methods 0.000 claims abstract description 9
- 230000016615 flocculation Effects 0.000 claims abstract description 9
- 238000004062 sedimentation Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 32
- 239000003480 eluent Substances 0.000 claims description 28
- 239000003960 organic solvent Substances 0.000 claims description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 23
- 239000002250 absorbent Substances 0.000 claims description 22
- 230000002745 absorbent Effects 0.000 claims description 22
- 235000019441 ethanol Nutrition 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
- 244000063299 Bacillus subtilis Species 0.000 claims description 21
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 10
- 238000004587 chromatography analysis Methods 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 7
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229920002401 polyacrylamide Polymers 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- -1 chloromethanes Alkane Chemical class 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- NBGBEUITCPENLJ-UHFFFAOYSA-N Bunazosin hydrochloride Chemical compound Cl.C1CN(C(=O)CCC)CCCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 NBGBEUITCPENLJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012065 filter cake Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract description 11
- 239000000843 powder Substances 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000000855 fermentation Methods 0.000 abstract description 6
- 230000004151 fermentation Effects 0.000 abstract description 6
- 238000000638 solvent extraction Methods 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 11
- PFRQBZFETXBLTP-RCIYGOBDSA-N 2-[(2e,6e,10e,14e,18e)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methyl-1,4-dihydronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C/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)C(=O)C2=C1 PFRQBZFETXBLTP-RCIYGOBDSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229930003448 Vitamin K Natural products 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229960001866 silicon dioxide Drugs 0.000 description 7
- 235000019168 vitamin K Nutrition 0.000 description 7
- 239000011712 vitamin K Substances 0.000 description 7
- 150000003721 vitamin K derivatives Chemical class 0.000 description 7
- 229940046010 vitamin k Drugs 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- ABSPRNADVQNDOU-UHFFFAOYSA-N Menaquinone 1 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(C)C(=O)C2=C1 ABSPRNADVQNDOU-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 235000019175 phylloquinone Nutrition 0.000 description 4
- 239000011772 phylloquinone Substances 0.000 description 4
- MBWXNTAXLNYFJB-NKFFZRIASA-N phylloquinone Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-NKFFZRIASA-N 0.000 description 4
- 229960001898 phytomenadione Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- 230000004097 bone metabolism Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 235000013557 nattō Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 235000019155 vitamin A Nutrition 0.000 description 2
- 239000011719 vitamin A Substances 0.000 description 2
- 229940045997 vitamin a Drugs 0.000 description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003883 substance clean up Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
- 239000011652 vitamin K3 Substances 0.000 description 1
- 229940041603 vitamin k 3 Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Claims (9)
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113004134A (zh) * | 2021-03-04 | 2021-06-22 | 中国科学院合肥物质科学研究院 | 一种利用棕榈油提取物分离纯化发酵液中维生素k2的方法 |
CN114538589A (zh) * | 2022-02-25 | 2022-05-27 | 中国科学院合肥物质科学研究院 | 一种富集发酵液中萜类化合物的方法及其使用的纤维素基絮凝剂 |
CN115304464A (zh) * | 2022-09-02 | 2022-11-08 | 新拓洋生物工程有限公司 | 一种维生素k2(35)的提取方法 |
CN116283531A (zh) * | 2023-02-27 | 2023-06-23 | 广东新达瑞生物科技有限公司 | 一种维生素k2的萃取工艺 |
Citations (4)
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US20110201054A1 (en) * | 2009-02-18 | 2011-08-18 | Viridis Biopharma Pvt Ltd | Process for improved recovery of fermentation products from intracellular and extracellular presence |
CN103571897A (zh) * | 2013-10-29 | 2014-02-12 | 中国科学院合肥物质科学研究院 | 一种维生素k2及其制备方法 |
CN103898175A (zh) * | 2014-03-31 | 2014-07-02 | 广东双骏生物科技有限公司 | 一种纳豆枯草芽孢杆菌以及由该菌株提纯维生素甲萘醌-7的方法 |
CN106631748A (zh) * | 2016-12-16 | 2017-05-10 | 中国科学院合肥物质科学研究院 | 一种分离纯化纳豆芽孢杆菌中维生素k2的方法 |
-
2019
- 2019-05-30 CN CN201910462407.9A patent/CN110041184B/zh active Active
Patent Citations (5)
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US20110201054A1 (en) * | 2009-02-18 | 2011-08-18 | Viridis Biopharma Pvt Ltd | Process for improved recovery of fermentation products from intracellular and extracellular presence |
CN103571897A (zh) * | 2013-10-29 | 2014-02-12 | 中国科学院合肥物质科学研究院 | 一种维生素k2及其制备方法 |
CN103898175A (zh) * | 2014-03-31 | 2014-07-02 | 广东双骏生物科技有限公司 | 一种纳豆枯草芽孢杆菌以及由该菌株提纯维生素甲萘醌-7的方法 |
CN104262129A (zh) * | 2014-03-31 | 2015-01-07 | 广东双骏生物科技有限公司 | 一种纳豆枯草芽孢杆菌以及由该菌株提纯维生素甲萘醌-7的方法 |
CN106631748A (zh) * | 2016-12-16 | 2017-05-10 | 中国科学院合肥物质科学研究院 | 一种分离纯化纳豆芽孢杆菌中维生素k2的方法 |
Non-Patent Citations (1)
Title |
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ZHIWEI FANG,等: "A simple and efficient preparative procedure for menaquinone-7 from Bacillus subtilis (natto) using two-stage extraction followed by microporous resins", 《PROCESS BIOCHEMISTRY》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113004134A (zh) * | 2021-03-04 | 2021-06-22 | 中国科学院合肥物质科学研究院 | 一种利用棕榈油提取物分离纯化发酵液中维生素k2的方法 |
CN113004134B (zh) * | 2021-03-04 | 2023-04-07 | 中国科学院合肥物质科学研究院 | 一种利用棕榈油提取物分离纯化发酵液中维生素k2的方法 |
CN114538589A (zh) * | 2022-02-25 | 2022-05-27 | 中国科学院合肥物质科学研究院 | 一种富集发酵液中萜类化合物的方法及其使用的纤维素基絮凝剂 |
CN114538589B (zh) * | 2022-02-25 | 2023-08-25 | 中国科学院合肥物质科学研究院 | 一种富集发酵液中萜类化合物的方法及其使用的纤维素基絮凝剂 |
CN115304464A (zh) * | 2022-09-02 | 2022-11-08 | 新拓洋生物工程有限公司 | 一种维生素k2(35)的提取方法 |
CN116283531A (zh) * | 2023-02-27 | 2023-06-23 | 广东新达瑞生物科技有限公司 | 一种维生素k2的萃取工艺 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
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Denomination of invention: A Purification Method for Vitamin Methylnaphthoquinon-7 Effective date of registration: 20230418 Granted publication date: 20220201 Pledgee: Fujian Straits bank Limited by Share Ltd. Fuqing branch Pledgor: FUJIAN KANGHONG BIOTECHNOLOGY Co.,Ltd. Registration number: Y2023350000121 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20220201 Pledgee: Fujian Straits bank Limited by Share Ltd. Fuqing branch Pledgor: FUJIAN KANGHONG BIOTECHNOLOGY Co.,Ltd. Registration number: Y2023350000121 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A purification method for vitamin menaquinone-7 Granted publication date: 20220201 Pledgee: Fujian Straits bank Limited by Share Ltd. Fuqing branch Pledgor: FUJIAN KANGHONG BIOTECHNOLOGY Co.,Ltd. Registration number: Y2024350000040 |