CN116283531A - Extraction process of vitamin K2 - Google Patents
Extraction process of vitamin K2 Download PDFInfo
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- CN116283531A CN116283531A CN202310169337.4A CN202310169337A CN116283531A CN 116283531 A CN116283531 A CN 116283531A CN 202310169337 A CN202310169337 A CN 202310169337A CN 116283531 A CN116283531 A CN 116283531A
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- Prior art keywords
- vitamin
- chromatographic column
- drying
- liquid
- extraction
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- 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 68
- DKHGMERMDICWDU-GHDNBGIDSA-N menaquinone-4 Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 DKHGMERMDICWDU-GHDNBGIDSA-N 0.000 title claims abstract description 68
- 235000019143 vitamin K2 Nutrition 0.000 title claims abstract description 68
- 239000011728 vitamin K2 Substances 0.000 title claims abstract description 68
- 238000000605 extraction Methods 0.000 title claims abstract description 33
- 239000007788 liquid Substances 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000001035 drying Methods 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 22
- 239000000284 extract Substances 0.000 claims abstract description 18
- 239000000843 powder Substances 0.000 claims abstract description 18
- 230000001580 bacterial effect Effects 0.000 claims abstract description 16
- 238000000855 fermentation Methods 0.000 claims abstract description 16
- 230000004151 fermentation Effects 0.000 claims abstract description 16
- 238000003756 stirring Methods 0.000 claims abstract description 14
- 238000000926 separation method Methods 0.000 claims abstract description 12
- 241000233866 Fungi Species 0.000 claims abstract description 11
- 239000002674 ointment Substances 0.000 claims abstract description 10
- 238000011049 filling Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000010451 perlite Substances 0.000 claims description 6
- 235000019362 perlite Nutrition 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
- 229940011051 isopropyl acetate Drugs 0.000 claims description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000012065 filter cake Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 241000894006 Bacteria Species 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
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 241001052560 Thallis Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000002308 calcification Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010257 thawing Methods 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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention provides an extraction process of vitamin K2, which comprises the following steps: (1) Adding a filter aid into the vitamin K2 fermentation liquid, uniformly stirring, and then carrying out solid-liquid separation to obtain bacterial residues rich in vitamin K2; (2) drying and crushing fungus residues to obtain fungus powder; (3) Filling the bacterial powder into a chromatographic column, and compacting the bacterial powder by using clean gas; (4) Adding organic solvent for extraction from a chromatographic column feed inlet at a set flow rate, collecting effluent liquid of the chromatographic column to obtain vitamin K2 high-concentration extract liquid, collecting 0.4-0.6 times of the volume of the chromatographic column, stopping adding the organic solvent, and drying the liquid in the chromatographic column by using clean gas; (5) Concentrating the high-concentration vitamin K2 extract to obtain vitamin K2 ointment. Compared with the traditional stirring extraction process, the process provided by the invention has the advantages of less extraction solvent consumption, high extraction yield, high vitamin K2 ointment content and the like, and has great industrial value.
Description
Technical Field
The invention relates to the technical field of vitamin extraction, in particular to an extraction process of vitamin K2.
Background
Vitamin K2 is referred to as menadione for short, is a fat-soluble vitamin and plays an important role in preventing osteoporosis and cardiovascular calcification. With the increasing market demand, achieving industrialization of vitamin K2 and reducing production costs have become a focus of attention. Vitamin K2 is now produced mainly by chemical synthesis and biological fermentation. The chemical method has the defects of more byproducts, low yield, serious environmental pollution and the like, and the product has cis-isomer with low activity, so the product is not popular in the market. The vitamin K2 with high activity can only be obtained by a microbial fermentation method, so that the fermentation method has wider application prospect.
In the prior art, an organic solvent extraction method is mostly adopted for extracting vitamin K2 from fermentation broth, so that vitamin K2 is transferred from cells to an organic solvent in an intracellular manner, and the subsequent purification process is facilitated. Chinese patent CN109824496 discloses a method for extracting vitamin K2, which comprises filtering fermentation broth with ceramic membrane, concentrating, breaking cell wall by nitrogen ion beam bombardment, adding 5-25 times of ethanol, stirring, extracting, centrifuging, and collecting supernatant to obtain vitamin K2 extractive solution. Chinese patent CN106631748 discloses a method for preparing vitamin K2, which comprises the steps of adopting centrifugal solid-liquid separation, repeatedly freezing and thawing wet cells to break walls, adding n-hexane, stirring and extracting to obtain vitamin K2 extract, purifying and separating the vitamin K2 extract with a resin column and a silica gel column, and crystallizing to obtain pure product of K2. The vitamin K2 fermentation unit is very low (the titer is 100-200 mg/L), so that the content of thalli is not high after solid-liquid separation. In the traditional organic solvent stirring extraction process, in order to ensure the extraction yield, 4-6 times of solvent is generally added for extraction for 2-3 times, so that the volume of an extraction liquid is overlarge, the product content is very low, the enrichment of other fat-soluble metabolites in cells is serious, and the difficulty of the subsequent purification process is increased.
Disclosure of Invention
The invention provides an extraction process of vitamin K2, which solves the defects of high extraction solvent amount and low extraction yield of the existing vitamin K2 extraction process.
The technical scheme of the invention is realized as follows:
an extraction process of vitamin K2 comprises the following steps:
(1) Adding a filter aid into the vitamin K2 fermentation liquid, uniformly stirring, and then carrying out solid-liquid separation to obtain bacterial residues rich in vitamin K2;
(2) Drying and crushing fungus residues to obtain fungus powder;
(3) Filling the bacterial powder into a chromatographic column, and compacting the bacterial powder by using clean gas;
(4) Adding organic solvent for extraction from a chromatographic column feed inlet at a set flow rate, opening a discharge valve of the chromatographic column, collecting effluent liquid of the chromatographic column to obtain vitamin K2 high-concentration extract liquid, collecting 0.4-0.6 times of the volume of the chromatographic column, stopping adding the organic solvent, and drying the liquid in the chromatographic column by using clean gas to finish extraction;
(5) And (3) carrying out vacuum concentration on the high-concentration vitamin K2 extract to obtain vitamin K2 ointment.
Further, in the step (1), the filter aid comprises perlite or diatomite, and the added mass of the filter aid is 2% -4% of the mass of the vitamin K2 fermentation broth.
Further, in the step (1), the solid-liquid separation adopts plate-frame filtration or centrifugal separation.
Further, in the step (2), the fungus dreg is dried by adopting any one of blast drying, vacuum drying and flash evaporation drying, and the drying temperature is 60-80 ℃.
Further, in the step (3), the height-to-diameter ratio of the chromatographic column is 3:1-5:1.
Further, the clean gas in step (3) and step (4) comprises nitrogen.
Further, the organic solvent in the step (4) includes any one of ethanol, isopropanol, acetone, ethyl acetate, isopropyl acetate, butyl acetate, n-hexane and n-heptane.
Further, the organic solvent is ethyl acetate or acetone.
Further, the flow rate of the organic solvent added in the step (4) is 0.25-1.0 BV/h.
Further, the flow rate of the organic solvent was 0.5BV/h.
Further, the concentration in the step (5) is vacuum concentration.
The invention has the beneficial effects that: compared with the traditional stirring extraction process, the method has the advantages of less consumption of extraction solvent, high extraction yield, high content of vitamin K2 ointment and the like, and is a production process with great industrialized value.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
An extraction process of vitamin K2 comprises the following steps:
(1) Adding a filter aid into the vitamin K2 fermentation liquid, uniformly stirring, and then carrying out solid-liquid separation to obtain bacterial residues rich in vitamin K2;
(2) Drying and crushing fungus residues to obtain fungus powder;
(3) Filling the bacterial powder into a chromatographic column, and compacting the bacterial powder by using clean gas;
(4) Adding organic solvent for extraction from a chromatographic column feed inlet at a set flow rate, opening a discharge valve of the chromatographic column, collecting effluent liquid of the chromatographic column to obtain vitamin K2 high-concentration extract liquid, collecting 0.4-0.6 times of the volume of the chromatographic column, stopping adding the organic solvent, and drying the liquid in the chromatographic column by using clean gas to finish extraction;
(5) And (3) carrying out vacuum concentration on the high-concentration vitamin K2 extract to obtain vitamin K2 ointment.
Further, in the step (1), the filter aid comprises perlite or diatomite, and the added mass of the filter aid is 2% -4% of the mass of the vitamin K2 fermentation broth.
Further, in the step (1), the solid-liquid separation adopts plate-frame filtration or centrifugal separation.
Further, in the step (2), the fungus dreg is dried by adopting any one of blast drying, vacuum drying and flash evaporation drying, and the drying temperature is 60-80 ℃.
Further, in the step (3), the height-to-diameter ratio of the chromatographic column is 3:1-5:1.
Further, the clean gas in step (3) and step (4) comprises nitrogen.
Further, the organic solvent in the step (4) includes any one of ethanol, isopropanol, acetone, ethyl acetate, isopropyl acetate, butyl acetate, n-hexane and n-heptane.
Further, the organic solvent is ethyl acetate or acetone.
Further, the flow rate of the organic solvent added in the step (4) is 0.25-1.0 BV/h.
Further, the flow rate of the organic solvent was 0.5BV/h.
Further, the concentration in the step (5) is vacuum concentration.
Example 1
30L of vitamin K2 fermentation broth with the titer of 133.2mg/L is added with 600g of perlite, and after uniform stirring, the mixture is filtered by a plate frame to obtain 3.26kg of filter cake.
And (3) drying the filter cake for 26 hours by blowing, wherein the drying temperature is 60 ℃, and crushing to obtain 1.89kg of vitamin K2 bacteria powder.
After transferring the dry bacterial powder method into a stainless steel chromatographic column (3000 mL), the bacterial powder is compacted by compressed nitrogen.
Opening a feed valve of the stainless steel chromatographic column, adding ethyl acetate according to the flow rate of 1500mL/h, opening a discharge valve, and starting to collect and extract when the liquid flows out; and (3) closing an ethyl acetate feed valve, opening compressed nitrogen, drying ethyl acetate in the column by pressing, and combining to obtain 1860mL of vitamin K2 high-concentration extract with the titer of 2143.6mg/L.
The high-concentration vitamin K2 extract is concentrated to dryness in vacuum at the temperature of 45 ℃ to obtain 36.7g of vitamin K2 ointment with the mass content of 10.86 percent and the process yield of 99.8 percent.
Example 2
500L of vitamin K2 fermentation broth with the titer of 141.4mg/L is added with 12kg of perlite, and after uniform stirring, the mixture is filtered by a plate frame to obtain 52.6kg of filter cake.
And (3) drying the filter cake at 60 ℃ in a vacuum bipyramid mode for 18 hours, and crushing to obtain 33.2kg of vitamin K2 bacteria powder.
The bacterial powder is transferred into a stainless steel chromatographic column (60L) by a dry method, and then the bacterial powder is compacted by compressed nitrogen.
Opening a feed valve of the stainless steel chromatographic column, adding acetone according to the flow rate of 30L/h, opening a discharge valve, and starting to collect the extraction liquid when the liquid flows out; and (3) closing an ethyl acetate feed valve, opening compressed nitrogen, pressing acetone in the column to dry, and combining to obtain 38.6L of vitamin K2 high-concentration extract with the titer of 1813.7mg/L.
And concentrating the high-concentration vitamin K2 extract to dryness in vacuum at 50 ℃ to obtain 635.6g of vitamin K2 ointment, wherein the mass content is 11.02%, and the process yield is 99.35%.
Comparative experiments
According to the method of Chinese patent CN 109824496. 50L of vitamin K2 fermentation broth with the titer of 127.2mg/L is added with 1000g of perlite, and after uniform stirring, the mixture is filtered by a plate frame to obtain 5.27kg of filter cake. The filter cake was added with 20L ethanol, stirred and extracted for 4 hours, and filtered to obtain 21.5L of primary extract with a titer of 221.1mg/L. Adding 20L ethanol again, stirring and extracting for 4h, and filtering to obtain secondary extract 20.6L with a potency of 62.3mg/L. Combining the two extracts 42.1L, concentrating to dryness at 55deg.C under vacuum to obtain 292.6g of vitamin K2 ointment with mass content of 2.17% and process yield of 95.2%.
Compared with the traditional stirring extraction process, the method has the advantages of less consumption of extraction solvent, high extraction yield, high content of vitamin K2 ointment and the like, and is a production process with great industrial value.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (10)
1. An extraction process of vitamin K2 is characterized in that: the method comprises the following steps:
(1) Adding a filter aid into the vitamin K2 fermentation liquid, uniformly stirring, and then carrying out solid-liquid separation to obtain bacterial residues rich in vitamin K2;
(2) Drying and crushing fungus residues to obtain fungus powder;
(3) Filling the bacterial powder into a chromatographic column, and compacting the bacterial powder by using clean gas;
(4) Adding organic solvent for extraction from a chromatographic column feed inlet at a set flow rate, opening a discharge valve of the chromatographic column, collecting effluent liquid of the chromatographic column to obtain vitamin K2 high-concentration extract liquid, collecting 0.4-0.6 times of the volume of the chromatographic column, stopping adding the organic solvent, and drying the liquid in the chromatographic column by using clean gas to finish extraction;
(5) Concentrating the high-concentration vitamin K2 extract to obtain vitamin K2 ointment.
2. The process for extracting vitamin K2 as claimed in claim 1, wherein: the filter aid in the step (1) comprises perlite or diatomite, and the added mass of the filter aid is 2% -4% of the mass of the vitamin K2 fermentation liquor.
3. The process for extracting vitamin K2 as claimed in claim 1, wherein: and (3) carrying out solid-liquid separation in the step (1) by adopting plate frame filtration or centrifugal separation.
4. The process for extracting vitamin K2 as claimed in claim 1, wherein: and (3) drying the fungus residues in the step (2) by adopting any one of blast drying, vacuum drying and flash evaporation drying, wherein the drying temperature is 60-80 ℃.
5. The process for extracting vitamin K2 as claimed in claim 1, wherein: the aspect ratio of the chromatographic column in the step (3) is 3:1-5:1.
6. The process for extracting vitamin K2 as claimed in claim 1, wherein: the clean gas in step (3) and step (4) comprises nitrogen.
7. The process for extracting vitamin K2 as claimed in claim 1, wherein: the organic solvent in the step (4) comprises any one of ethanol, isopropanol, acetone, ethyl acetate, isopropyl acetate, butyl acetate, n-hexane and n-heptane.
8. The process for extracting vitamin K2 as claimed in claim 1, wherein: the flow rate of the organic solvent added in the step (4) is 0.25-1.0 BV/h.
9. The process for extracting vitamin K2 as claimed in claim 8, wherein: the adding flow rate of the organic solvent is 0.5BV/h.
10. The process for extracting vitamin K2 as claimed in claim 1, wherein: concentrating in the step (5) to vacuum concentration.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310169337.4A CN116283531A (en) | 2023-02-27 | 2023-02-27 | Extraction process of vitamin K2 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310169337.4A CN116283531A (en) | 2023-02-27 | 2023-02-27 | Extraction process of vitamin K2 |
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| CN116283531A true CN116283531A (en) | 2023-06-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310169337.4A Pending CN116283531A (en) | 2023-02-27 | 2023-02-27 | Extraction process of vitamin K2 |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006325597A (en) * | 2006-06-15 | 2006-12-07 | Nippon Seibutsu Kagaku Kenkyusho:Kk | Method for recovery of vitamin k2 |
| CN106046023A (en) * | 2016-06-10 | 2016-10-26 | 山东新时代药业有限公司 | Extraction method of tacrolimus |
| CN106631748A (en) * | 2016-12-16 | 2017-05-10 | 中国科学院合肥物质科学研究院 | Method for separating and purifying vitamin K2 in bacillus subtilis natto |
| CN109824496A (en) * | 2019-03-12 | 2019-05-31 | 中国科学院合肥物质科学研究院 | A method of the extraction purification farnoquinone from broken wall bafillus natto thallus |
| CN110041184A (en) * | 2019-05-30 | 2019-07-23 | 福建康鸿生物科技有限公司 | A kind of method of purification of vitamin menaquinone-7 |
| CN110964029A (en) * | 2019-12-19 | 2020-04-07 | 鲁南制药集团股份有限公司 | Pretreatment method of epothilone B fermentation liquor |
| CN113308500A (en) * | 2021-06-22 | 2021-08-27 | 山东润德生物科技有限公司 | Method for extracting vitamin K2 from fermentation liquor |
-
2023
- 2023-02-27 CN CN202310169337.4A patent/CN116283531A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006325597A (en) * | 2006-06-15 | 2006-12-07 | Nippon Seibutsu Kagaku Kenkyusho:Kk | Method for recovery of vitamin k2 |
| CN106046023A (en) * | 2016-06-10 | 2016-10-26 | 山东新时代药业有限公司 | Extraction method of tacrolimus |
| CN106631748A (en) * | 2016-12-16 | 2017-05-10 | 中国科学院合肥物质科学研究院 | Method for separating and purifying vitamin K2 in bacillus subtilis natto |
| CN109824496A (en) * | 2019-03-12 | 2019-05-31 | 中国科学院合肥物质科学研究院 | A method of the extraction purification farnoquinone from broken wall bafillus natto thallus |
| CN110041184A (en) * | 2019-05-30 | 2019-07-23 | 福建康鸿生物科技有限公司 | A kind of method of purification of vitamin menaquinone-7 |
| CN110964029A (en) * | 2019-12-19 | 2020-04-07 | 鲁南制药集团股份有限公司 | Pretreatment method of epothilone B fermentation liquor |
| CN113308500A (en) * | 2021-06-22 | 2021-08-27 | 山东润德生物科技有限公司 | Method for extracting vitamin K2 from fermentation liquor |
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