CN113173847A - Method for separating nervonic acid based on simulated moving bed - Google Patents
Method for separating nervonic acid based on simulated moving bed Download PDFInfo
- Publication number
- CN113173847A CN113173847A CN202110491561.6A CN202110491561A CN113173847A CN 113173847 A CN113173847 A CN 113173847A CN 202110491561 A CN202110491561 A CN 202110491561A CN 113173847 A CN113173847 A CN 113173847A
- Authority
- CN
- China
- Prior art keywords
- pump
- extract
- mobile phase
- nervonic acid
- moving bed
- 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.)
- Pending
Links
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 title claims abstract description 40
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 title claims abstract description 40
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 19
- 241000219226 Acer truncatum Species 0.000 claims abstract description 23
- 238000010828 elution Methods 0.000 claims abstract description 17
- 239000003480 eluent Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 28
- 230000014759 maintenance of location Effects 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002994 raw material Substances 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 238000005086 pumping Methods 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 8
- 150000007524 organic acids Chemical class 0.000 abstract description 2
- 241000270666 Testudines Species 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 241001143500 Aceraceae Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004641 brain development Effects 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 235000020774 essential nutrients Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002339 glycosphingolipids Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 210000000944 nerve tissue Anatomy 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000001082 somatic cell Anatomy 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The invention discloses a method for separating nervonic acid based on a simulated moving bed, and belongs to the field of organic acid separation. The method comprises the following steps: getting Acer truncatum oil; extracting the acer truncatum buge oil obtained in step S1 with an organic solvent to obtain an extract; dissolving by using a first eluent to obtain an elution dissolving solution; injecting the solution into a simulated moving bed, and separating by using a second eluent to obtain a solution containing nervonic acid; concentrating and drying to obtain nervonic acid. The invention can safely and efficiently separate high-purity nervonic acid from acer truncatum buge oil.
Description
Technical Field
The invention belongs to the field of organic acid separation, and particularly relates to a method for separating nervonic acid based on a simulated moving bed.
Background
Acer truncatum Bunge is a deciduous tree of Aceraceae, mechanical genus, and is named because the wing fruit shape is similar to the ancient gold ingot in China.
The seed kernel of Acer truncatum Bunge is rich in oil and protein, and the oil is rich in essential fatty acid and fat-soluble vitamin for human body. In recent years, researches show that the acer truncatum buge oil not only has an inhibiting effect on tumor cells, but also can promote the growth of new tissues and has a repairing effect on somatic cells. Research shows that the oil content of the acer truncatum bunge kernel is 42.6 percent, 12 fatty acids are detected, wherein the content of unsaturated fatty acids is 92 percent, and the content of nervonic acid is 5.52 percent. The nervonic acid contained in the kernel has various health care functions closely related to the health of human bodies, so the resource is very precious.
Nervonic Acid (NA) was earlier extracted from turtle oil of deep-sea turtles, so called selacholic acid, which was first found in nervous tissues of mammals, and is called Nervonic acid. Nervonic acid has high content in animal and human nerve tissues and brain tissues, and is an important component of biological membranes. Nervonic acid exists in white matter of human brain mainly in the form of glycosphingolipid and sphingomyelin, is a core natural component of nerve fiber and nerve cell of brain, and is an essential nutrient for brain development and maintenance.
The nervonic acid is mainly from animal brains and turtle oil in the past, and the extraction of the nervonic acid from the raw materials is difficult, particularly the raw materials are lack, and the cost is high. The acer truncatum buge oil not only contains a plurality of unsaturated fatty acids, but also has considerable nervonic acid content, thereby being a favorable resource for developing nervonic acid. However, the existing technology for separating nervonic acid from acer truncatum has not been mature or has poor separation effect.
Disclosure of Invention
In order to solve at least one of the above technical problems, the technical solution adopted by the present invention is as follows:
the invention provides a method for separating nervonic acid based on a simulated moving bed, which comprises the following steps:
s1, obtaining acer truncatum oil;
s2, extracting the acer truncatum buge oil obtained in the step S1 by using an organic solvent, and esterifying nervonic acid in the acer truncatum buge oil through transesterification reaction to obtain an extract; wherein, the esterification refers to ethyl esterification or methyl esterification.
S3, dissolving the extract obtained in the step S2 by using a first eluent to obtain an elution dissolving solution;
s4, injecting the elution dissolving solution obtained in the step S3 into a simulated moving bed, and separating by using a second eluent to obtain a solution containing nervonic acid;
s5, concentrating and drying the nervus containing solution obtained in the step S4 to obtain nervonic acid.
In some embodiments of the invention, the simulated moving bed is composed of 4 to 12 chromatographic columns 1 connected end to end, a raw material pump 2, a weak retention component pump 3, a mobile phase pump 4 and an extract pump 5 are sequentially connected between any two chromatographic columns along the clockwise direction, at least one chromatographic column is arranged between any two of the raw material pump 2, the weak retention component pump 3, the mobile phase pump 4 and the extract pump 5, and the raw material pump 2, the weak retention component pump 3, the mobile phase pump 4 and the extract pump 5 are respectively connected with a sample feed inlet, a residue outlet, a mobile phase inlet and an extract outlet.
Thus, further, in step S4, the elution solution obtained in step S3 is injected into the sample feed port via the raw material pump 2, flows clockwise, and flows through the weak retention component pump 3, mobile phase pump 4, and extract pump 5 in this order; and injecting the second eluent into the mobile phase inlet through a mobile phase pump 4, leading the weakly retained component out of the remainder outlet through a weakly retained component pump 3, and pumping the solution containing the nervonic acid out of the extract outlet through an extract pump 5.
In some embodiments of the invention, the simulated moving bed comprises 4 chromatography columns 1, wherein one chromatography column is separated between any two of the raw material pump 2, the weak retention component pump 3, the mobile phase pump 4 and the extract pump 5.
In other embodiments of the invention, the simulated moving bed comprises 8 chromatography columns 1, wherein any two of the feed pump 2, weak retention component pump 3, mobile phase pump 4, and extract pump 5 are separated by two chromatography columns.
In still other embodiments of the present invention, the simulated moving bed comprises 12 chromatography columns 1, wherein three chromatography columns are spaced between any two of the feed pump 2, weak retention component pump 3, mobile phase pump 4, and extract pump 5.
Further, preferably, a constant flow pump 6 is connected between the mobile phase pump 4 and the chromatographic column in the flow direction of the mobile phase.
In some embodiments of the present invention, the organic solvent is selected from ethyl ether, petroleum ether, n-hexane or a mixed solvent composed thereof.
In some embodiments of the present invention, the organic solvent is n-hexane or a mixed solvent composed thereof.
In some embodiments of the present invention, the first elution solution is a mixed solution of ethanol and ammonia water. In some embodiments of the invention, in the first elution solution, the ratio of ethanol to ammonia water is 20-30: 5 to 10.
In some embodiments of the invention, the second elution solution is 60-100% ethanol. In some embodiments of the invention, the second elution solution is 75% ethanol.
In the invention, the acer truncatum buge oil is acer truncatum buge seed kernel oil.
The invention has the advantages of
Compared with the prior art, the invention has the following beneficial effects:
the invention realizes the high-purity separation of the nervonic acid by using the simulated moving bed for the first time, and the purity of the nervonic acid obtained by separation is up to more than 96 percent.
The reagent used in the method is safe and nontoxic, and can be directly used for preparing food-grade products.
Drawings
Figure 1 shows a schematic diagram of a simulated moving bed of example 1 of the present invention. Wherein 1 denotes a column, 2 denotes a raw material pump, 3 denotes a weak retention component pump, 4 denotes a mobile phase pump, 5 denotes an extract pump, and 6 denotes a constant flow pump.
Fig. 2 shows a schematic diagram of the separation of nervonic acid from acer truncatum buge oil by using a simulated moving bed in example 2 of the present invention. Wherein component a represents a weakly retained component and component B represents a solution containing nervonic acid.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects solved by the present invention more apparent, the present invention is further described in detail below with reference to the following embodiments.
Examples
The following examples are used herein to demonstrate preferred embodiments of the invention. It will be appreciated by those of skill in the art that the techniques disclosed in the examples which follow represent techniques discovered by the inventor to function in the invention, and thus can be considered to constitute preferred modes for its practice. Those of skill in the art should, in light of the present disclosure, appreciate that many changes can be made in the specific embodiments which are disclosed and still obtain a like or similar result without departing from the spirit or scope of the invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs and the disclosures and references cited herein and the materials to which they refer are incorporated by reference.
Those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments of the invention described herein. Such equivalents are intended to be encompassed by the following claims.
The experimental procedures in the following examples are conventional unless otherwise specified. The instruments used in the following examples are, unless otherwise specified, laboratory-standard instruments; the test materials used in the following examples were purchased from a conventional biochemical reagent store unless otherwise specified.
Example 1 simulated moving bed for isolation of nervonic acid
The embodiment provides a simulated moving bed for separating nervonic acid, as shown in fig. 1, the simulated moving bed is composed of 8 chromatographic columns 1 connected end to end, and according to the clockwise direction, a raw material pump 2, a weak retention component pump 3, a mobile phase pump 4 and an extract pump 5 are sequentially connected to the second two chromatographic columns, and the raw material pump 2, the weak retention component pump 3, the mobile phase pump 4 and the extract pump 5 are respectively connected with a sample feed inlet, a residue outlet, a mobile phase inlet and an extract outlet.
In the flowing direction of the mobile phase (clockwise), a constant flow pump 6 is connected between the mobile phase pump 4 and the chromatographic column and used for controlling the flow of the mobile phase.
The simulated moving bed is also provided with a multi-channel rotary valve which is switched clockwise and is used for controlling the opening and closing of each inlet and each outlet. The multi-channel rotary valve is connected with a computer control system, and can save manpower and achieve separation standardization through computer program operation.
Example 2 isolation of nervonic acid from Acer Truncatum Bunge oil Using the simulated moving bed of example 1
In this example, nervonic acid was separated from Acer Truncatum Bunge oil using a simulated moving bed designed in example 1.
Firstly, extracting acer truncatum oil from acer truncatum kernels; then n-hexane is used for extracting the acer truncatum buge oil obtained in the step S1 to obtain an extract; the extract was dissolved in an eluent (ethanol, ammonia water 20: 7) to obtain an eluent solution.
Injecting an elution dissolving solution into a sample feeding hole through a raw material pump 2, enabling the elution dissolving solution to flow clockwise, and enabling the elution dissolving solution to sequentially flow through a weak retention component pump 3, a mobile phase pump 4 and an extract pump 5; eluent (75% ethanol) is injected into the mobile phase inlet through a mobile phase pump, the weak retention component is led out from the residue outlet through a weak retention component pump 3, and the solution containing nervonic acid is extracted from the extract outlet through an extract pump 5. Concentrating and drying the solution containing nervonic acid to obtain nervonic acid with the purity as high as 96.7 percent. A schematic of the separation process is shown in figure 2.
All documents referred to herein are incorporated by reference into this application as if each were individually incorporated by reference. Furthermore, it should be understood that various changes and modifications of the present invention can be made by those skilled in the art after reading the above teachings of the present invention, and these equivalents also fall within the scope of the present invention as defined by the appended claims.
Claims (10)
1. A method for separating nervonic acid based on a simulated moving bed is characterized by comprising the following steps:
s1, obtaining acer truncatum oil;
s2, extracting the acer truncatum buge oil obtained in the step S1 by using an organic solvent, and esterifying nervonic acid in the acer truncatum buge oil through transesterification reaction to obtain an extract;
s3, dissolving the extract obtained in the step S2 by using a first eluent to obtain an elution dissolving solution;
s4, injecting the elution dissolving solution obtained in the step S3 into a simulated moving bed, and separating by using a second eluent to obtain a solution containing nervonic acid;
s5, concentrating and drying the nervus containing solution obtained in the step S4 to obtain nervonic acid.
2. The method according to claim 1, wherein the simulated moving bed is composed of 4 to 12 chromatographic columns (1) connected end to end, a raw material pump (2), a weak retention component pump (3), a mobile phase pump (4) and an extract pump (5) are sequentially connected between any two chromatographic columns along the clockwise direction, at least one chromatographic column is arranged between any two of the raw material pump (2), the weak retention component pump (3), the mobile phase pump (4) and the extract pump (5), and the raw material pump (2), the weak retention component pump (3), the mobile phase pump (4) and the extract pump (5) are respectively connected with a sample feed port, a residue outlet, a mobile phase inlet and an extract outlet.
3. The method according to claim 2, wherein in step S4, the elution solution obtained in step S3 is injected into the sample feed port via a raw material pump (2), flows clockwise, and flows through a weak retention component pump (3), a mobile phase pump (4), and an extract pump (5) in this order; and injecting the second eluent into the mobile phase inlet through a mobile phase pump (4), leading the weak retention component out of the remainder outlet through a weak retention component pump (3), and pumping the solution containing the nervonic acid out of the extract outlet through an extract pump (5).
4. The method according to claim 2, wherein the simulated moving bed comprises 8-12 chromatographic columns (1), wherein two chromatographic columns are separated between any two of the raw material pump (2), the weak retention component pump (3), the mobile phase pump (4) and the extract pump (5).
5. The method according to claim 2, wherein the simulated moving bed comprises 12 chromatographic columns (1), wherein three chromatographic columns are arranged between any two of the raw material pump (2), the weak retention component pump (3), the mobile phase pump (4) and the extract pump (5).
6. The method according to any one of claims 2 to 5, characterized in that a constant flow pump (6) is further connected between the mobile phase pump (4) and the chromatography column in the mobile phase flow direction.
7. The method according to claim 6, wherein the organic solvent is selected from the group consisting of diethyl ether, petroleum ether, n-hexane, and a mixed solvent thereof.
8. The method according to claim 7, wherein the first elution solution is a mixed solution of ethanol and ammonia water.
9. The method according to claim 8, wherein the ratio of ethanol to ammonia water in the first elution solution is 20-30: 5 to 10.
10. The method of claim 8, wherein the second elution solution is 60-100% ethanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110491561.6A CN113173847A (en) | 2021-05-06 | 2021-05-06 | Method for separating nervonic acid based on simulated moving bed |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110491561.6A CN113173847A (en) | 2021-05-06 | 2021-05-06 | Method for separating nervonic acid based on simulated moving bed |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113173847A true CN113173847A (en) | 2021-07-27 |
Family
ID=76928894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110491561.6A Pending CN113173847A (en) | 2021-05-06 | 2021-05-06 | Method for separating nervonic acid based on simulated moving bed |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113173847A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5770088A (en) * | 1992-06-30 | 1998-06-23 | Daicel Chemical Industries, Ltd. | Simulated moving bed chromatographic separation process |
| CN101092344A (en) * | 2007-07-06 | 2007-12-26 | 杨凌七彩生物科技有限公司 | Method for extracting nervonic acid from oil of Mono Maple by using technique of molecular distillation |
| CN101575282A (en) * | 2009-06-15 | 2009-11-11 | 中国科学院山西煤炭化学研究所 | Method for using molecular distillation to extract nervonic acid from acer truncatum buge oil |
-
2021
- 2021-05-06 CN CN202110491561.6A patent/CN113173847A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5770088A (en) * | 1992-06-30 | 1998-06-23 | Daicel Chemical Industries, Ltd. | Simulated moving bed chromatographic separation process |
| CN101092344A (en) * | 2007-07-06 | 2007-12-26 | 杨凌七彩生物科技有限公司 | Method for extracting nervonic acid from oil of Mono Maple by using technique of molecular distillation |
| CN101575282A (en) * | 2009-06-15 | 2009-11-11 | 中国科学院山西煤炭化学研究所 | Method for using molecular distillation to extract nervonic acid from acer truncatum buge oil |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104529772B (en) | A kind of simulated moving bed chromatography prepares high-purity EPA ester and the method for DHA ester monomer | |
| CN105911131B (en) | The detection method of phospholipid molecule in salmon | |
| CN102277230B (en) | Method of optimum rapid solvent extracting treatment for raising extraction amount of microalgae grease | |
| CN104293874B (en) | A kind of method for preparing free astaxanthin | |
| CN112592268B (en) | Method for separating EPA (eicosapentaenoic acid) in fish oil by using continuous chromatographic system | |
| CN105198885A (en) | Compound communesin I with anti-arrhythmias activity, and preparation method and application thereof | |
| CN107200767A (en) | A kind of preparation method of blood-sugar decreasing active Corosolic acid | |
| CN1958555A (en) | Method for preparing salviol acid A | |
| CN115010596A (en) | Method for enriching eicosapentaenoic acid in fish oil raw material | |
| CN106632577A (en) | Ursane triterpenoid saponin in masson pine twigs and preparation process thereof | |
| CN1284760C (en) | Preparation method of natural crystalized gingerol | |
| CN107709346A (en) | For the method for the isoprene component for separating guayule rubber | |
| CN101347490B (en) | Extract of rape pollen with broken wall and purification method and use thereof | |
| CN113173847A (en) | Method for separating nervonic acid based on simulated moving bed | |
| CN106912750A (en) | A kind of method for removing sterol in plant-feed insect man-made feeds | |
| CN111440157A (en) | Method for simultaneously separating schaftoside, viscapine-2 and ecdysone and application | |
| CN111012810A (en) | Preparation method of unsaponifiable matter in ginseng seed oil | |
| CN113698981A (en) | Production method of modified wood frog oil | |
| CN108794443A (en) | A method of preparing high-purity cyanidenon | |
| CN113754526A (en) | High-purity coenzyme Q10 purification process | |
| CN113440551A (en) | Salvia miltiorrhiza residue extract with antioxidant activity and application thereof | |
| Yingying et al. | Physiological evidence for the relationship between unsaturated fatty acid and cell permeability in extracellular polysaccharide synthesis and secretion Agaricus bitorquis (Quél.) Sacc. Chaidam | |
| CN111044626B (en) | Preparation method of ginseng flower extract | |
| Choopani et al. | An Efficient Method for Extraction and Enrichment of γ-Linolenic Acid (GLA) from Spirulina | |
| CN109609472A (en) | A kind of utilization method of soya whey wastewater |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210727 |
|
| RJ01 | Rejection of invention patent application after publication |