CN112679561A - Preparation method of glycerol glucoside crystal - Google Patents
Preparation method of glycerol glucoside crystal Download PDFInfo
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- CN112679561A CN112679561A CN202011584478.5A CN202011584478A CN112679561A CN 112679561 A CN112679561 A CN 112679561A CN 202011584478 A CN202011584478 A CN 202011584478A CN 112679561 A CN112679561 A CN 112679561A
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 239000013078 crystal Substances 0.000 title claims abstract description 30
- 229930182478 glucoside Natural products 0.000 title claims abstract description 19
- -1 glycerol glucoside Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000012528 membrane Substances 0.000 claims abstract description 33
- 239000000284 extract Substances 0.000 claims abstract description 27
- 239000000815 hypotonic solution Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 21
- 238000011033 desalting Methods 0.000 claims abstract description 19
- 230000001954 sterilising effect Effects 0.000 claims abstract description 19
- 238000004659 sterilization and disinfection Methods 0.000 claims abstract description 16
- 230000002335 preservative effect Effects 0.000 claims abstract description 12
- 239000000049 pigment Substances 0.000 claims abstract description 11
- 239000003755 preservative agent Substances 0.000 claims abstract description 11
- 238000004108 freeze drying Methods 0.000 claims abstract description 9
- 229920005862 polyol Polymers 0.000 claims abstract description 3
- 150000003077 polyols Chemical class 0.000 claims abstract description 3
- 239000011347 resin Substances 0.000 claims description 51
- 229920005989 resin Polymers 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 36
- 238000000605 extraction Methods 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 10
- 239000000287 crude extract Substances 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical group CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 8
- 238000002390 rotary evaporation Methods 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000035614 depigmentation Effects 0.000 claims description 3
- 230000003204 osmotic effect Effects 0.000 claims description 3
- 241000195493 Cryptophyta Species 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000001471 micro-filtration Methods 0.000 claims description 2
- 238000001728 nano-filtration Methods 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 238000002203 pretreatment Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000000108 ultra-filtration Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 9
- 235000016425 Arthrospira platensis Nutrition 0.000 description 6
- 240000002900 Arthrospira platensis Species 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229940082787 spirulina Drugs 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000516 sunscreening agent Substances 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241000192656 Nostoc Species 0.000 description 1
- 241000192707 Synechococcus Species 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000490 cosmetic additive Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 230000001033 osmoprotective effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention discloses a preparation method of a glycerol glucoside crystal, which comprises the following steps: extracting in the microalgae rich in GG by using a hypotonic solution, removing pigment from the obtained hypotonic extract, desalting, sterilizing by a membrane sterilization mode, concentrating the GG sterilization solution, adding a polyol preservative into the concentrated solution, and freeze-drying to obtain GG crystals.
Description
Technical Field
The invention belongs to the technical field of preparation of glycerol glucoside, and particularly relates to a preparation method of a glycerol glucoside crystal.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
GG is a substance formed by combining glycerol molecules and glucose molecules by glycosidic bonds, the configuration of the glucose molecules and the positions of the glycerol molecules are divided into six types, six types are identified at present, the natural configurations are 2 alpha and 2 beta configurations, and the 2 alpha configuration has multiple functions and is widely applied. It is an osmoprotective substance synthesized by microorganisms under the condition of stress, is also a macromolecular stabilizer, can be used for long-term storage of protein drugs and the like, is a good cosmetic additive, and has the effects of moisturizing, resisting oxidation, resisting aging and the like. Since GG has utility in various fields, it is required to be a high-purity GG having good storage stability and containing no impurities, decomposition products, or the like. GG crystals are easier to transport and store than aqueous solutions. However, GG is apt to absorb moisture and hardly provides crystals, and it is difficult to obtain an aqueous GG solution in general and to satisfy the demand for large-scale supply on an industrial scale.
Disclosure of Invention
In view of the technical problems in the prior art, the present invention aims to provide a method for preparing glycerol glucoside crystals.
In order to solve the technical problems, the technical scheme of the invention is as follows:
a preparation method of glycerol glucoside crystals comprises the following steps:
extracting the microalgae cells rich in GG by using a hypotonic solution, removing pigments from the obtained hypotonic extract, desalting, sterilizing by a membrane sterilization mode, concentrating the GG sterilization solution, adding a polyol preservative into the concentrated solution, and freeze-drying to obtain GG crystals.
Compared with the prior art, the beneficial technical effects of one or more of the embodiments of the invention are as follows:
adding polyalcohol preservative such as 1, 2-pentanediol into the GG crude extract to enable the concentration of the polyalcohol preservative to be 0.05% -10%, wherein the 1, 2-pentanediol is a humectant with excellent performance and has a preservative effect, so that a preservative-free product can be prepared, and allergy caused by the preservative is reduced; can improve the water resistance of the formula of the sunscreen product, and can be used in various skin care products such as skin cream, eye cream, skin lotion, infant care products, sunscreen products and the like. The microbial safety of the raw materials can be fully ensured by adding the 1, 2-pentanediol.
Desalting the resin can obtain high-yield crystals.
The desalting method comprises passing negative resin and positive resin, removing anion and cation to increase crystallization yield, concentrating, drying, and crystallizing to obtain 95% (the ratio of negative resin to positive resin is 400: 250) with crystallization period of 1-5 days.
The product is prepared by passing positive resin and then passing negative resin (the mass ratio of negative resin to positive resin is 250: 400), removing cations and then removing anions, and concentrating and drying to obtain the product with the yield of 85% and the crystallization period of 6-15 days.
The obtained GG crude extract was dehydrated by rotary evaporation and then freeze-dried to obtain a glycerol glucoside crystal.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. 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 application belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present application. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
A preparation method of glycerol glucoside crystals comprises the following steps:
adding the hypotonic solution into the microalgae rich in GG for extraction to obtain hypotonic extract rich in GG, pigment and salt;
removing pigment from the low-permeability extraction liquid by adopting a membrane separation method, and desalting by using resin to obtain GG crude extract;
filtering the GG crude extract into a GMP workshop in a membrane sterilization mode to form GG sterilization liquid;
concentrating GG sterilization liquid to obtain GG crude extract concentrated solution;
adding polyalcohol preservative into the GG concentrated solution to enable the concentration of the polyalcohol preservative to be 0.05-10%, and freeze-drying to obtain GG crystals.
In some embodiments, the microalgae species is multicladium, nostoc, synechococcus, cryptophyceae, spirulina, etc., the species is not limited, and further preferably spirulina.
In some embodiments, the hypotonic solution is a substance capable of altering the osmotic pressure of a cell;
further, the concentration of the hypotonic solution is 0-300 mM;
further, the concentration of the hypotonic solution is 50-100 mM.
For example, a substance capable of changing the cell osmotic pressure is added at a concentration of 0 to 300mM, and the substance may be sodium chloride, potassium chloride, or the like, or may be a hypotonic solution as long as it can induce GG synthesis reaction.
In some embodiments, the pretreatment method for extracting the microalgae rich in GG to obtain the hypotonic extract is as follows: dewatering the collected microalgae mud rich in GG, mixing the microalgae mud with a low-permeability solution according to the volume ratio of 1:1, extracting, separating the microalgae mud with the low-permeability solution to obtain solid microalgae mud and GG aqueous solution, extracting for 1-8 times in the way, and collecting extract liquor after each extraction or combining the extract liquor after multiple extractions to obtain the low-permeability extract liquor.
In some embodiments, the mass ratio of GG-enriched microalgae to hypotonic solution is less than 2;
furthermore, the mass ratio of the microalgae rich in GG to the hypotonic solution is 1: 0.5-1.2.
In some embodiments, the membrane separation filtration depigmentation method is: and (3) performing decoloration treatment on the obtained extract liquor by adopting a membrane concentration method, wherein the membrane aperture is 100-1000 (Dalton).
Further, the membrane separation and filtration depigmentation method comprises microfiltration, ultrafiltration and nanofiltration.
In some embodiments, the resin is used for desalting by first passing through the anionic resin and then passing through the cationic resin, wherein the mass ratio of the anionic resin to the cationic resin is 50-500: 100-1000.
Further, the crystallization period is 1-5 days, and the ratio of the anion resin: the mass ratio of the cationic resin is 400: 250.
in some embodiments, the resin is used for desalting by passing the cation resin and then passing the anion resin, wherein the anion resin: the mass ratio of the cationic resin is 250: 400, the crystallization period is 6 to 15 days.
Further, the membrane sterilization of this step has a pore size of 0.1-0.22 μm.
In some embodiments, the crude extract concentrate has a GG concentration of 50-98%.
Further, the crude extract concentrate is obtained by the following method: and (3) rotationally evaporating and concentrating the GG sterilization liquid under the conditions of low-temperature heating and vacuum.
Further, the low-temperature heating temperature is 50-60 ℃.
Furthermore, the vacuum degree of the rotary evaporation is-0.02 to-0.04 MPa.
Example 1
Taking a hypotonic extraction liquid rich in GG: mixing the collected microalgae spirulina rich in GG with hypotonic solution water for extraction, wherein the mass ratio of the microalgae to the hypotonic solution is 1:1, and filtering the microalgae to obtain a hypotonic extract mixture rich in GG, pigment and salt. The obtained extract liquor is subjected to decoloration treatment by adopting a membrane separation method, and the membrane separation, filtration and decoloration method comprises the following steps: decolorizing the obtained extractive solution with membrane concentration method, wherein the membrane aperture is 2500 daltons.
Desalting the obtained extract liquor by adopting a resin method, wherein the desalting method comprises the steps of firstly passing through negative resin and then passing through positive resin, firstly removing anions and then removing cations, and the negative resin: the mass ratio of the positive resin is 400: 250, obtaining GG with the mass concentration of 30 percent after concentration, concentrating the GG by rotary evaporation under the conditions that the temperature is 50 ℃ and the vacuum degree is-0.02 to-0.04 MPa until the GG mass concentration is 95.3 percent, adding 1,2 pentanediol (0.05 percent is 1, and the 2 pentanediol is the concentration after being added into the concentrated solution) with the mass concentration of 0.05 percent, and obtaining GG crystals after freeze-drying treatment. The GG crystallization period obtained at this time was 2 days, the purity was 97.5%, and the recovery rate in the whole process was 95%.
Example 2
Taking a hypotonic extraction liquid rich in GG: mixing and extracting the collected spirulina rich in GG with a hypotonic solution-potassium chloride solution, wherein the concentration of the potassium chloride solution is 0.2mM, the mass ratio of the microalgae to the hypotonic solution is 1:1, and filtering the microalgae to obtain a hypotonic extract mixture rich in GG, pigment and salt. The obtained extract liquor is subjected to decoloration treatment by adopting a membrane separation method, and the membrane separation, filtration and decoloration method comprises the following steps: and performing decoloration treatment on the obtained extract liquor by adopting a membrane concentration method, wherein the membrane aperture is 1000 daltons.
Desalting the obtained extract liquor by adopting a resin method, wherein the desalting method comprises the steps of firstly passing through cation resin and then passing through anion resin, and the anion resin: the mass ratio of the cationic resin is 250: 400. removing anions and cations, concentrating to obtain GG with the mass concentration of 30%, performing rotary evaporation concentration at the temperature of 50 ℃ and the vacuum degree of-0.02 to-0.04 MPa until the mass concentration of GG is 87.6%, adding 1,2 pentanediol (0.2% is 1, and 2 pentanediol is the concentration after being added into the concentrated solution) with the mass concentration of 2%, and performing freeze-drying treatment to obtain GG crystals. The GG crystallization period obtained at this time was 14 days, the purity was 65.5%, and the recovery rate in the whole process was 69.7%.
Example 3
Taking a hypotonic extraction liquid rich in GG: mixing and extracting collected spirulina rich in GG with sodium chloride, wherein the concentration of the sodium chloride solution is 0.4mM, the mass ratio of the microalgae to the hypotonic solution is 1:1, and filtering the microalgae to obtain a hypotonic extract mixture rich in GG, pigment and salt. The obtained extract liquor is subjected to decoloration treatment by adopting a membrane separation method, and the membrane separation, filtration and decoloration method comprises the following steps: and performing decoloration treatment on the obtained extract liquor by adopting a membrane concentration method, wherein the membrane aperture is 7000 daltons.
Desalting the obtained extract liquor by adopting a resin method, wherein the desalting method comprises the steps of firstly passing through negative resin and then passing through positive resin, firstly removing anions and then removing cations, and the negative resin: the mass ratio of the positive resin is 300: 500, obtaining GG with the mass concentration of 30 percent after concentration, concentrating the GG by rotary evaporation at the temperature of 50 ℃ and the vacuum degree of-0.02 to-0.04 MPa until the GG mass concentration is 75.7 percent, adding 1,2 pentanediol with the mass concentration of 1 percent, and obtaining GG crystals after freeze-drying treatment. The GG crystallization period obtained at this time was 12 days, the purity was 63.5%, and the recovery rate in the whole process was 73.4%.
Example 4
Taking a hypotonic extraction liquid rich in GG: mixing and extracting the collected spirulina rich in GG with hypotonic solution water, wherein the mass ratio of the microalgae to the hypotonic solution is 1:1, and filtering the microalgae to obtain a hypotonic extract mixture rich in GG, pigment and salt. The obtained extract liquor is subjected to decoloration treatment by adopting a membrane separation method, and the membrane separation, filtration and decoloration method comprises the following steps: and performing decoloration treatment on the obtained extract liquor by adopting a membrane concentration method, wherein the membrane aperture is 4000 daltons.
Desalting the obtained extract liquor by adopting a resin method, wherein the desalting method comprises the steps of firstly passing through negative resin and then passing through positive resin, firstly removing anions and then removing cations, and the negative resin: the mass ratio of the positive resin is 300: 500, obtaining GG with the mass concentration of 30 percent after concentration, concentrating the GG by rotary evaporation at the temperature of 50 ℃ and the vacuum degree of-0.02 to-0.04 MPa until the GG mass concentration is 84.3 percent, adding 1,2 pentanediol with the mass concentration of 0.5 percent, and obtaining GG crystals after freeze-drying treatment. The GG crystallization period obtained at this time was 5 days, the purity was 96.5%, and the recovery rate in the whole process was 82.7%.
The above description is only a preferred embodiment of the present application and is not intended to limit the present application, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application shall be included in the protection scope of the present application.
Claims (10)
1. A method for preparing a glycerol glucoside crystal is characterized in that: the method comprises the following steps:
the method comprises the steps of extracting microalgae rich in GG by using a hypotonic solution, removing pigments from obtained hypotonic extract, desalting, sterilizing by a membrane sterilization mode, concentrating GG sterilization liquid, adding a polyol preservative into the concentrated solution, and freeze-drying to obtain GG crystals.
2. The method for producing a glycerol glucoside crystal according to claim 1, wherein: the specific method comprises the following steps:
adding the hypotonic solution into the microalgae rich in GG for extraction to obtain hypotonic extract rich in GG, pigment and salt;
removing pigment from the low-permeability extraction liquid by adopting a membrane separation method, and desalting by using resin to obtain GG crude extract;
filtering the GG crude extract into a GMP workshop in a membrane sterilization mode to form GG sterilization liquid;
concentrating GG sterilization liquid to obtain GG crude extract concentrated solution;
adding polyalcohol preservative into the GG concentrated solution to enable the concentration of the polyalcohol preservative to be 0.05-10%, and freeze-drying to obtain GG crystals.
3. The method for producing a glycerol glucoside crystal according to claim 2, wherein: the hypotonic solution is a substance capable of altering the osmotic pressure of cells;
further, the concentration of the hypotonic solution is 0-300 mM;
further, the concentration of the hypotonic solution is 50-100 mM;
further, the concentration mode is rotary evaporation concentration;
further, the polyalcohol preservative is 1, 2-pentanediol.
4. The method for producing a glycerol glucoside crystal according to claim 1, wherein: the pretreatment method for extracting the microalgae rich in GG to obtain the hypotonic extract liquid comprises the following steps: dehydrating the collected microalgae mud rich in GG, mixing and extracting the microalgae mud and a hypotonic solution in proportion, and separating algae mud from water to obtain microalgae mud solid and GG water solution;
further, the repeated extraction times are 1-8 times, and the extraction liquid after each extraction is collected or the extraction liquids after multiple extractions are combined to obtain the hypotonic extraction liquid.
5. The method for producing a glycerol glucoside crystal according to claim 1, wherein: the mass ratio of the microalgae rich in GG to the hypotonic solution is less than 2;
further, the mass ratio of the microalgae rich in GG to the hypotonic solution is 1: 0.5-1.2;
further, the membrane separation, filtration and decoloration method comprises the following steps: performing decoloration treatment on the obtained extract liquor by adopting a membrane concentration method, wherein the membrane aperture is 100-1000 daltons;
further, the membrane separation and filtration depigmentation method comprises microfiltration, ultrafiltration and nanofiltration.
6. The method for producing a glycerol glucoside crystal according to claim 1, wherein: in the method for desalting by adopting the resin, the mass ratio of the anion resin to the cation resin is 50-500: 100-1000;
further, the method for desalting by adopting the resin comprises the steps of firstly passing through the anion resin and then passing through the cation resin, wherein the crystallization period is 1-5 days, and the anion resin: the mass ratio of the cationic resin is 400: 250.
7. the method for producing a glycerol glucoside crystal according to claim 1, wherein: the pore diameter of the sterilization membrane is 0.1-0.22 micron.
8. The method for producing a glycerol glucoside crystal according to claim 1, wherein: in the concentrated solution, the concentration of GG is 50-98%.
9. The method for producing a glycerol glucoside crystal according to claim 8, wherein: the crude extraction concentrated solution is obtained by the following method: and (3) rotationally evaporating and concentrating the GG sterilization liquid under the conditions of low-temperature heating and vacuum.
10. The method for producing a glycerol glucoside crystal according to claim 9, wherein: the low-temperature heating temperature is 50-60 ℃;
furthermore, the vacuum degree of the rotary evaporation is-0.02 to-0.04 MPa.
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| CN116943430A (en) * | 2022-04-20 | 2023-10-27 | 中国科学院青岛生物能源与过程研究所 | Four-step method for separating and purifying glyceroglycosides |
| CN116947934A (en) * | 2022-04-20 | 2023-10-27 | 中国科学院青岛生物能源与过程研究所 | A two-step method for separating and purifying glycerol glucoside |
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