CN115677468A - Method for purifying coenzyme Q10 - Google Patents
Method for purifying coenzyme Q10 Download PDFInfo
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- CN115677468A CN115677468A CN202211359710.4A CN202211359710A CN115677468A CN 115677468 A CN115677468 A CN 115677468A CN 202211359710 A CN202211359710 A CN 202211359710A CN 115677468 A CN115677468 A CN 115677468A
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- coenzyme
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- 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 title claims abstract description 42
- 235000017471 coenzyme Q10 Nutrition 0.000 title claims abstract description 42
- 229940110767 coenzyme Q10 Drugs 0.000 title claims abstract description 41
- 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 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 14
- 238000000926 separation method Methods 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 230000008025 crystallization Effects 0.000 claims abstract description 7
- 150000002632 lipids Chemical class 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 239000012046 mixed solvent Substances 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 230000001580 bacterial effect Effects 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 238000000855 fermentation Methods 0.000 claims description 9
- 230000004151 fermentation Effects 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 230000000813 microbial effect Effects 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 239000012296 anti-solvent Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 150000002576 ketones Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 230000005526 G1 to G0 transition Effects 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000010298 pulverizing process Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 9
- 238000000746 purification Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000000049 pigment Substances 0.000 abstract description 2
- 150000004053 quinones Chemical class 0.000 abstract description 2
- 238000011210 chromatographic step Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 241000191043 Rhodobacter sphaeroides Species 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 208000015606 cardiovascular system disease Diseases 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 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 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for purifying coenzyme Q10, and belongs to the technical field of compound separation. The method comprises the steps of pretreatment, extraction, chromatography and crystallization; the invention relates to a two-step separation and purification method, wherein the extraction step is mainly used for separating lipids, quinones and part of pigment impurities; the chromatographic step is mainly used for separating coenzyme Q10 and 5-demethyl coenzyme Q10 and similar coenzyme Q10 impurities; most of the impurities are removed after two-step separation, but the impurities are in a liquid state and need to be crystallized to become solid pure coenzyme Q10. The invention adopts the moving bed chromatography technology to realize the continuity of production; meanwhile, the yield is high, the solvent consumption is low, and the method is suitable for large-scale industrial application.
Description
Technical Field
The invention belongs to the technical field of compound separation, and particularly relates to a method for purifying coenzyme Q10.
Background
Coenzyme Q10 (ubiquinone), chemical name 2- [ (all-E) 3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10, 14,18,22,26,30,34,38-forty decenyl } -5,6-dimethoxy-3-methyl-p-benzoquinone. Coenzyme Q10 is involved in energy production and activation in human body cells, is widely used for treating cardiovascular system diseases in medicine, and is a substance with high commercial value. In addition, coenzyme Q10 is also widely applied to industries such as food (health products) and cosmetics.
The preparation method of the coenzyme Q10 mainly comprises three methods, namely an animal and plant tissue extraction method, a chemical synthesis method and a microbial fermentation method; the animal and plant tissue extraction method has complicated conditions and high cost; the chemical synthesis method needs less separation of cis-trans isomers and less separation components, and the microbial fermentation method is widely applied due to the advantages of low production cost, no isomer and the like.
However, the components of the microbial fermentation broth are complex, and the purification and extraction of coenzyme Q10 are difficult. At present, the method mainly comprises an alkali-alcohol saponification method, an alkalization saponification method, an acid purification method, an ultrasonic crushing method and supercritical CO 2 Extraction methods, and the like.
Wherein, the effect of purifying by adopting a chromatographic column is good, but industrialization is difficult to realize; because a large amount of impurities irreversibly adhere to the column with the use of the column, the chromatographically active sites are occupied, and the efficiency is greatly reduced.
Disclosure of Invention
The invention provides a method for purifying coenzyme Q10, which is a purification method with industrial value aiming at the coenzyme Q10 prepared by a microbial fermentation method.
The method for purifying the coenzyme Q10 comprises the following steps:
(1) Pretreatment: filtering the microbial fermentation liquor, and drying to obtain bacterial powder; pulverizing the fungus powder;
(2) Extraction: mixing and stirring the mixed solvent and the bacterial powder; then adding an anti-solvent, stirring again, standing, and taking an organic solution layer;
(3) And (3) chromatography: the organic solution layer is feeding liquid; introducing into a moving bed chromatography system, and collecting raffinate;
(4) And (3) crystallization: concentrating, crystallizing, washing and drying the raffinate to obtain the coenzyme Q10.
In particular, in the step (1), the powder is crushed to a particle size of less than or equal to 30 μm.
In particular, in the step (2), the mixed solvent is petroleum ether and
at least one mixed solvent of ethanol, acetone, acetonitrile, ethyl acetate, isopropanol and dipropylene glycol in a volume ratio of 10;
the volume mass ratio of the mixed solvent to the bacterial powder is 8-16.
In particular, in the step (2), organic acid with the mass of 2.6-3.8% of the bacterial powder is added into the mixed solvent; the organic acid is at least one of fumaric acid, maleic acid, acetic acid, citric acid or tartaric acid.
Specifically, in the step (2), the anti-solvent is water, and the volume ratio of the mixed solvent to the water is 10-16.
In particular, in the step (3), the eluent of the moving bed chromatography system is petroleum ether or C 6 -C 8 The saturated alkane of (2).
In particular, in the step (3), the stationary phase of the moving bed chromatography system is silica gel with a particle size of 10-100 μm.
In particular, in the step (3), the operation parameters of the moving bed chromatography system are controlled as follows:
the separation temperature is 0-30 deg.C, eluent flow rate is 2-10mL/min, feed liquid flow rate is 2-10mL/min, extraction liquid flow rate is 1-5mL/min, raffinate flow rate is 1-5mL/min, and switching time is 1-5min.
In particular, the raffinate in the step (4) is concentrated and then added with a solvent for crystallization;
the solvent is ketone, alcohol, lipid and/or ether organic solvent.
The organic solvents of ketones, alcohols, lipids and/or ethers include but are not limited to: acetone, butanone, ethanol, isopropanol, dipropylene glycol, methyl formate, ethyl formate, propyl formate, ethyl acetate, methyl acetate, oleyl ether, diethyl ether, isopropyl ether, diisopropyl ether, ethyl butyl ether.
Compared with the prior art, the invention has the beneficial effects that:
the invention relates to a two-step separation and purification method, wherein the step (2) is mainly used for separating lipids, quinones and partial pigment impurities; the step (3) is mainly used for separating coenzyme Q10, 5-demethyl coenzyme Q10 and similar coenzyme Q10 impurities; most impurities are removed after two-step separation, but the coenzyme Q10 is in a liquid state and can become solid pure coenzyme Q10 only after the step (4); meanwhile, the step (4) can be further purified, and impurities remained in the step (2) and the step (3) are removed.
The invention finds that the effect of separation can be amplified by adding an organic acid to adjust the pH in step (2), and that the addition of an inorganic acid has a negative effect on the separation as shown in some experimental results.
The invention adopts the moving bed chromatography technology to realize the continuity of production; meanwhile, the yield is high, the solvent consumption is low, and the method is suitable for large-scale industrial application.
Detailed Description
For a better understanding of the present invention, the present invention is further described in conjunction with the following specific examples, wherein the terminology used in the examples is for the purpose of describing particular embodiments only and is not intended to limit the scope of the present invention.
The microbial fermentation broth used in the present invention is derived from Rhodobacter sphaeroides (Rhodobacter sphaeroides) fermentation broth (coenzyme Q10 content tested 4.9%).
The method for purifying the coenzyme Q10 comprises the following steps:
(1) Pretreatment: filtering the microbial fermentation liquor, and drying to obtain bacterial powder; pulverizing the fungus powder with a superfine pulverizer;
(2) Extraction: mixing and stirring the mixed solvent and the bacterial powder; then adding an anti-solvent, stirring again, standing for layering, and taking an organic solution layer;
adding organic acid with the mass of 2.6-3.8% of the bacterial powder into the mixed solvent; the organic acid is at least one of fumaric acid, maleic acid, acetic acid, citric acid or tartaric acid.
The anti-solvent is water, and the volume ratio of the mixed solvent to the water is 10-16.
The mixed solvent is a mixed solvent of petroleum ether and at least one of ethanol, acetone, acetonitrile, ethyl acetate, isopropanol and dipropylene glycol in a volume ratio of 10-6;
the volume mass ratio of the mixed solvent to the bacterial powder is 8-16.
(3) And (3) chromatography: the organic solution layer is feeding liquid; introducing into a moving bed chromatographic system, and taking raffinate;
the eluent of the moving bed chromatographic system is petroleum ether or C 6 -C 8 Is a saturated alkane.
The stationary phase of the moving bed chromatographic system is silica gel with the particle size of 10-100 mu m.
The operating parameters of the moving bed chromatography system are controlled as follows:
the separation temperature is 0-30 deg.C, eluent flow rate is 2-10mL/min, feed liquid flow rate is 2-10mL/min, extraction liquid flow rate is 1-5mL/min, raffinate flow rate is 1-5mL/min, and switching time is 1-5min.
(4) And (3) crystallization: concentrating the raffinate, adding a solvent at 40-60 ℃ until the solid is just dissolved, cooling to-5 ℃, cooling for crystallization for 12-36 hours, filtering, washing a filter cake with water, and drying the product in vacuum.
Concentrating raffinate, and adding a solvent for crystallization;
the solvent is organic solvent of ketone, alcohol, lipid and/or ether.
Specific technical parameters are shown in table 1 below.
TABLE 1
For the coenzyme Q10 solid prepared in each example, the detection method of the coenzyme Q10 in the 2020 pharmacopoeia is adopted for detection, wherein:
example 1 coenzyme Q10 purity of 99.9%, yield of 99.3%;
example 2 coenzyme Q10 purity of 99.8%, yield of 98.9%;
example 3 coenzyme Q10 purity 99.8%, yield 99.2%;
example 4 coenzyme Q10 purity was 99.8%, yield 98.9%;
example 5 coenzyme Q10 purity of 99.9%, yield of 99.1%.
The above detailed description is specific to one possible embodiment of the present invention, and the embodiment is not intended to limit the scope of the present invention, and all equivalent implementations or modifications without departing from the scope of the present invention should be included in the technical scope of the present invention.
Claims (9)
1. The method for purifying coenzyme Q10 is characterized by comprising the following steps:
(1) Pretreatment: filtering the microbial fermentation liquor, and drying to obtain bacterial powder; pulverizing the fungus powder;
(2) Extraction: mixing and stirring the mixed solvent and the bacterial powder; then adding an anti-solvent, stirring again, standing, and taking an organic solution layer;
(3) And (3) chromatography: the organic solution layer is feeding liquid; introducing into a moving bed chromatographic system, and taking raffinate;
(4) And (3) crystallization: concentrating, crystallizing, washing and drying the raffinate to obtain the coenzyme Q10.
2. The method for purifying coenzyme Q10 according to claim 1, wherein in the step (1), the powder is pulverized to a particle size of 30 μm or less.
3. The method for purifying coenzyme Q10 according to claim 1, wherein in the step (2), the mixed solvent is petroleum ether and
at least one mixed solvent of ethanol, acetone, acetonitrile, ethyl acetate, isopropanol and dipropylene glycol in a volume ratio of 10;
the volume mass ratio of the mixed solvent to the bacterial powder is 8-16.
4. The method for purifying coenzyme Q10 according to claim 1, characterized in that in the step (2), an organic acid is added to the mixed solvent in an amount of 2.6 to 3.8% by mass of the fungal powder; the organic acid is at least one of fumaric acid, maleic acid, acetic acid, citric acid or tartaric acid.
5. The method for purifying coenzyme Q10 according to claim 1, wherein in the step (2), the anti-solvent is water, and the volume ratio of the mixed solvent to water is 10 to 16.
6. The method for purifying coenzyme Q10 according to claim 1, wherein in the step (3), the eluent of the moving bed chromatography system is petroleum ether or C 6 -C 8 Is a saturated alkane.
7. The method for purifying coenzyme Q10 according to claim 1, wherein in the step (3), the stationary phase of the moving bed chromatography system is silica gel having a particle size of 10 to 100 μm.
8. The method for purifying coenzyme Q10 according to claim 1, wherein in the step (3), the operating parameters of the moving bed chromatography system are controlled as follows:
the separation temperature is 0-30 deg.C, eluent flow rate is 2-10mL/min, feed liquid flow rate is 2-10mL/min, extraction liquid flow rate is 1-5mL/min, raffinate flow rate is 1-5mL/min, and switching time is 1-5min.
9. The method for purifying coenzyme Q10 according to claim 1, characterized in that the raffinate in the step (4) is concentrated and then crystallized by adding a solvent;
the solvent is ketone, alcohol, lipid and/or ether organic solvent.
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| CN202211359710.4A CN115677468A (en) | 2022-11-02 | 2022-11-02 | Method for purifying coenzyme Q10 |
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| CN202211359710.4A CN115677468A (en) | 2022-11-02 | 2022-11-02 | Method for purifying coenzyme Q10 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108017530A (en) * | 2017-12-12 | 2018-05-11 | 浙江大学 | A kind of method that Co-Q10 is continuously separated from bacteria residue |
| CN108084007A (en) * | 2017-12-12 | 2018-05-29 | 浙江大学 | A kind of method of Simulated Moving Bed Chromatography separation Co-Q10 and CoQ1 1 |
| CN108863743A (en) * | 2018-07-19 | 2018-11-23 | 浙江新和成股份有限公司 | The method for extraction and purification of Co-Q10 and Co-Q10 prepared therefrom |
| CN110465114A (en) * | 2019-08-23 | 2019-11-19 | 内蒙古金达威药业有限公司 | A kind of Simulation moving bed continuous chromatography chromatographic system and its application and the method for purifying Co-Q10 |
| CN113501752A (en) * | 2021-07-21 | 2021-10-15 | 山东泰和水处理科技股份有限公司 | Acid purification method of coenzyme Q10 |
-
2022
- 2022-11-02 CN CN202211359710.4A patent/CN115677468A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108017530A (en) * | 2017-12-12 | 2018-05-11 | 浙江大学 | A kind of method that Co-Q10 is continuously separated from bacteria residue |
| CN108084007A (en) * | 2017-12-12 | 2018-05-29 | 浙江大学 | A kind of method of Simulated Moving Bed Chromatography separation Co-Q10 and CoQ1 1 |
| CN108863743A (en) * | 2018-07-19 | 2018-11-23 | 浙江新和成股份有限公司 | The method for extraction and purification of Co-Q10 and Co-Q10 prepared therefrom |
| CN110465114A (en) * | 2019-08-23 | 2019-11-19 | 内蒙古金达威药业有限公司 | A kind of Simulation moving bed continuous chromatography chromatographic system and its application and the method for purifying Co-Q10 |
| CN113501752A (en) * | 2021-07-21 | 2021-10-15 | 山东泰和水处理科技股份有限公司 | Acid purification method of coenzyme Q10 |
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