CN109456359A - A method of isolating and purifying crude product L- ɑ-choline glycerophosphatide - Google Patents
A method of isolating and purifying crude product L- ɑ-choline glycerophosphatide Download PDFInfo
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- CN109456359A CN109456359A CN201811349079.3A CN201811349079A CN109456359A CN 109456359 A CN109456359 A CN 109456359A CN 201811349079 A CN201811349079 A CN 201811349079A CN 109456359 A CN109456359 A CN 109456359A
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- crude product
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- isopropanol
- acetone
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- 239000012043 crude product Substances 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229960001231 choline Drugs 0.000 title claims abstract description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 55
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000005406 washing Methods 0.000 claims abstract description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000746 purification Methods 0.000 claims abstract description 27
- 238000004090 dissolution Methods 0.000 claims abstract description 17
- 238000004821 distillation Methods 0.000 claims abstract description 15
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000002425 crystallisation Methods 0.000 claims abstract description 12
- 235000019441 ethanol Nutrition 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000005119 centrifugation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 7
- 229910001961 silver nitrate Inorganic materials 0.000 claims abstract description 7
- 238000012360 testing method Methods 0.000 claims abstract description 7
- 239000012535 impurity Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000012216 screening Methods 0.000 claims abstract description 4
- 229960004756 ethanol Drugs 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000004064 recycling Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 238000013517 stratification Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 2
- 239000013049 sediment Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000005416 organic matter Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- CTKINSOISVBQLD-GSVOUGTGSA-N (R)-Glycidol Chemical compound OC[C@@H]1CO1 CTKINSOISVBQLD-GSVOUGTGSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to field of new materials, and in particular to a method of crude product L- ɑ-choline glycerophosphatide is isolated and purified, includes the following steps: step S1, acetone washing；Step S2, isopropanol washing；Step S3, pure water dissolution；Step S4 by negative ion exchange resin column, and carries out silver nitrate reagent test；Step S5 is distilled off moisture, and is dissolved with ethyl alcohol；Step S6 is cooled to 30 DEG C, impurity screening；Step S7 after distillation, is cooled to 0 DEG C of crystallization；And step S8, centrifugation, drying obtain purification L- ɑ-choline glycerophosphatide, improve purity.
Description
Technical field
The present invention relates to field of new materials, and in particular to a kind of to isolate and purify crude product L- ɑ-choline glycerophosphatide side
Method.
Background technique
L- ɑ-choline glycerophosphatide (abbreviation L- ɑ-GPC) is high-new chiral medical basic material, is naturally occurring in vivo
The choline source of aqueous phospholipid metabolite and acetylcholine and Phosphatidylcholine biosynthesis has important alimentary health-care function
It is worth with medical application.Crude product L- α-choline glycerophosphatide is isolated and purified, medicinal rank is reached, is able to use
In clinical and preparation research, China's medical level can be improved, and effectively reduce due to imported L-α-choline glycerophosphatide medicine
Medicine valence caused by object preparation is higher.And crude product L- α-choline glycerophosphatide is during the preparation process, be generally easy to be mixed into chlorine from
Son (pass through (R)-glycidol prepare crude product), compatibility organic matter, in particular for the solvent of separating-purifying, as ethyl alcohol,
Acetone and isopropanol etc., these substances and L- α-choline glycerophosphatide compatibility are high, it is not easy to separate, seriously affect crude product
Purity and quality.
Summary of the invention
Crude product L- ɑ-choline glycerophosphatide method is isolated and purified the object of the present invention is to provide a kind of, to improve thick produce
The purity of product.
In order to solve the above-mentioned technical problems, the present invention provides crude product L- ɑ-choline glycerophosphatide method of purification, packets
Include following steps: step S1, acetone washing；Step S2, isopropanol washing；Step S3, pure water dissolution；Step S4, passes through feminine gender
Ion exchange resin column, and carry out silver nitrate reagent test；Step S5 is distilled off moisture, and is dissolved with ethyl alcohol；Step S6,
30 DEG C are cooled to, impurity screening；Step S7 after distillation, is cooled to 0 DEG C of crystallization；And step S8, centrifugation, drying.
Further, the method for acetone washing includes: step S11 in the step S1, by crude product L- ɑ-phosphoglycerol gallbladder
Alkali is added in acetone washing kettle, then adds acetone and is washed；Step S12, after acetone washing, stratification, i.e., on
Layer acetone, lower layer's crude product；Step S13, upper layer and lower layer are separated, and upper layer acetone is liquid phase, after distillation condensation, recycling,
To continue on for acetone washing；And step S14, lower coarse product are pumped into isopropanol washing kettle, wait isopropanol washing.
Further, the method that isopropanol washs in the step S2 includes: step S21, is added to isopropanol washing kettle different
Propyl alcohol is washed；Step S22, after acetone washing, stratification, i.e. upper layer isopropanol, lower layer's crude product；Step S23, will
Upper layer and lower layer separation, upper layer isopropanol are liquid phase, after distillation condensation, recycling, to continue on for isopropanol washing；And step
Rapid S24, lower layer's crude product enter in dissolution kettle, wait water dissolution.
Further, enough pure water are added into dissolution kettle, and stirs to crude product and all dissolves, form aqueous solution.
Further, aqueous solution is iterated through into negative ion exchange resin column, it is heavy not generate down to silver nitrate reagent test
Starch.
Further, moisture is distilled off in the step S5, and includes: step S51 with the method that ethyl alcohol dissolves, it will be water-soluble
Liquid is added in reaction kettle and is evaporated under reduced pressure, and to steam the moisture in solution, obtains crude product solid；Step S52, by crude product
Solid is transferred in dissolution kettle, and appropriate dehydrated alcohol is added, and is heated to 70 DEG C, stirring to crude product solid is all dissolved.
Further, in the step S7 distill after, be cooled to 0 DEG C crystallization method include: step S71, will be filtered
Filtrate is added in distillation crystallization kettle and dehydrated alcohol is distilled off；Step S72 is cooled to 0 DEG C and is crystallized.
Further, the mother liquor after centrifugation is suitable for by distillation, condensing recovery ethyl alcohol, to continue to use；Solid phase after centrifugation
It is directly dried, as purification L- ɑ-choline glycerophosphatide.
Further, step S5-S8 is repeated, so that purification L- ɑ-choline glycerophosphatide is finished product.
The invention has the advantages that method of purification of the invention is more by carrying out to crude product L- ɑ-choline glycerophosphatide
Secondary organic matter washing, plays the role of purification finally by dissolution, crystallisation by cooling；Purifying technique is simple, the medium in purification process
Object is easy recycling and utilizes again, reduces production cost；With with high purity, high-efficient, save the cost, environmentally protective, it is suitable for
The advantages of industrialized production.
Detailed description of the invention
Present invention will be further explained below with reference to the attached drawings and examples.
Fig. 1 is the process flow diagram of method of purification of the invention.
Specific embodiment
In conjunction with the accompanying drawings, the present invention is further explained in detail.
As shown in Figure 1, present embodiments providing a kind of method of purification of crude product L- ɑ-choline glycerophosphatide, including as follows
Step: step S1, acetone washing；Step S2, isopropanol washing；Step S3, pure water dissolution；Step S4, is handed over by negative ion
Resin column is changed, and carries out silver nitrate reagent test；Step S5 is distilled off moisture, and is dissolved with ethyl alcohol；Step S6, is cooled to
30 DEG C, impurity screening；Step S7 after distillation, is cooled to 0 DEG C of crystallization；And step S8, centrifugation, drying.Certainly, in order into one
Step improves purification L- ɑ-choline glycerophosphatide purity, it is only necessary to step S5-S8 be repeated several times.Now in purification process
Each process is specifically described.
(1) crude product L- ɑ-choline glycerophosphatide is added in acetone washing kettle, then adds acetone and is washed；?
It after acetone washing, is layered, i.e. upper layer acetone, lower layer's material (crude product L- ɑ-choline glycerophosphatide)；Upper layer acetone is liquid
Phase, after distillation condensation, recycling, to continue on for acetone washing.
(2) lower layer's material is pumped into isopropanol washing kettle, carries out isopropanol washing；Then it is layered, i.e., upper layer is different
Propyl alcohol, lower layer's material (L- ɑ-choline glycerophosphatide hydrochloride)；Upper layer isopropanol is liquid phase, after distillation condensation, recycling, with
Continue on for isopropanol washing.
(3) first lower layer's material is added in dissolution kettle, adds enough water, stirring to whole dissolutions forms aqueous solution, so
After aqueous solution can be iterated through to negative ion exchange resin column so that used by the aqueous solution of negative ion exchange resin column
Silver nitrate reagent test does not have white precipitate, illustrates that chloride ion all removes.
(4) aqueous solution is added in reaction kettle and is evaporated under reduced pressure, until condenser no liquid flows out, then explanation steams solution
In whole moisture, obtain crude product solid；Then crude product solid is transferred in dissolution kettle again, appropriate dehydrated alcohol is added,
70 DEG C are heated to, stirring to crude product solid is all dissolved.
(5) cooling 30 DEG C are cooled to extremely, to filter removal impurity；Then filtrate is added in distillation crystallization kettle, portion is evaporated off
Divide ethyl alcohol, the condensable recycling of the ethyl alcohol, and is back to production；Continue cool to 0 DEG C of crystallization；It is finally centrifuged, solid phase is taken to be done
It is dry, obtain purification L- ɑ-choline glycerophosphatide.And the mother liquor after being centrifuged can also be recycled by distilling, condensing.
In conclusion method of purification of the invention is washed by carrying out multiple organic matter to crude product L- ɑ-choline glycerophosphatide
It washs, to remove out the organic matter in product, plays the role of purification finally by dissolution, crystallisation by cooling, remove impurity and purification is situated between
Matter improves crude product L- ɑ-choline glycerophosphatide purity；Purifying technique is simple, and the dielectric object in purification process is easy recycling
It utilizes again, reduces production cost；With with high purity, high-efficient, save the cost, environmentally protective, it is suitable for industrialized production
The advantages of.
Taking the above-mentioned ideal embodiment according to the present invention as inspiration, through the above description, relevant staff is complete
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property range is not limited to the contents of the specification, it is necessary to which the technical scope thereof is determined according to the scope of the claim.
Claims (9)
1. a kind of method of purification of crude product L- ɑ-choline glycerophosphatide, which comprises the steps of:
Step S1, acetone washing；
Step S2, isopropanol washing；
Step S3, pure water dissolution；
Step S4 by negative ion exchange resin column, and carries out silver nitrate reagent test；
Step S5 is distilled off moisture, and is dissolved with ethyl alcohol；
Step S6 is cooled to 30 DEG C, impurity screening；
Step S7 after distillation, is cooled to 0 DEG C of crystallization；And
Step S8, centrifugation, drying.
2. method of purification according to claim 1, which is characterized in that
The method of acetone washing includes: in the step S1
Crude product L- ɑ-choline glycerophosphatide is added in acetone washing kettle, then adds acetone and washed by step S11；
Step S12, after acetone washing, stratification, i.e. upper layer acetone, lower layer's crude product；
Step S13, upper layer and lower layer are separated, and upper layer acetone is liquid phase, after distillation condensation, recycling, to continue on for acetone
Washing；And
Step S14, lower coarse product are pumped into isopropanol washing kettle, wait isopropanol washing.
3. method of purification according to claim 2, which is characterized in that
The method of isopropanol washing includes: in the step S2
Step S21 is added isopropanol to isopropanol washing kettle and is washed；
Step S22, after acetone washing, stratification, i.e. upper layer isopropanol, lower layer's crude product；
Step S23, upper layer and lower layer are separated, and upper layer isopropanol is liquid phase, and after distillation condensation, recycling is different to continue on for
Propanol rinse；And
Step S24, lower layer's crude product enter in dissolution kettle, wait water dissolution.
4. method of purification according to claim 3, which is characterized in that
Enough pure water are added into dissolution kettle, and stirs to crude product and all dissolves, form aqueous solution.
5. method of purification according to claim 4, which is characterized in that
Aqueous solution is iterated through into negative ion exchange resin column, so that silver nitrate reagent test does not generate sediment.
6. method of purification according to claim 5, which is characterized in that
Moisture is distilled off in the step S5, and includes: with the method that ethyl alcohol dissolves
Aqueous solution is added in reaction kettle and is evaporated under reduced pressure by step S51, and to steam the moisture in solution, it is solid to obtain crude product
Body；
Crude product solid is transferred in dissolution kettle by step S52, and appropriate dehydrated alcohol is added, and is heated to 70 DEG C, stirring to crude product
Solid all dissolves.
7. method of purification according to claim 1, which is characterized in that
In the step S7 distill after, be cooled to 0 DEG C crystallization method include:
Filtered filtrate is added in distillation crystallization kettle and dehydrated alcohol is distilled off by step S71；
Step S72 is cooled to 0 DEG C and is crystallized.
8. method of purification according to claim 1, which is characterized in that
Mother liquor after centrifugation is suitable for by distillation, condensing recovery ethyl alcohol, to continue to use；
Solid phase after centrifugation is directly dried, as purification L- ɑ-choline glycerophosphatide.
9. method of purification according to claim 1, which is characterized in that
Step S5-S8 is repeated, so that purification L- ɑ-choline glycerophosphatide.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811349079.3A CN109456359A (en) | 2018-11-13 | 2018-11-13 | A method of isolating and purifying crude product L- ɑ-choline glycerophosphatide |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811349079.3A CN109456359A (en) | 2018-11-13 | 2018-11-13 | A method of isolating and purifying crude product L- ɑ-choline glycerophosphatide |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103087091A (en) * | 2011-10-27 | 2013-05-08 | 上海秀新臣邦医药科技有限公司 | L-alpha-choline glycerophosphate synthesis method |
| CN103304594A (en) * | 2013-06-18 | 2013-09-18 | 上海科利生物医药有限公司 | Preparation method of L-alpha-glycerophosphoryl choline |
| CN104193778A (en) * | 2014-08-14 | 2014-12-10 | 苏州富士莱医药股份有限公司 | Crystallization method of liquid glycerylphosphorylcholine |
| CN104356160A (en) * | 2014-11-05 | 2015-02-18 | 合肥创新医药技术有限公司 | Purification process of L-alpha-glycerophosphoryl choline |
| CN108329344A (en) * | 2017-12-29 | 2018-07-27 | 中山百灵生物技术有限公司 | A kind of purification process of glycerophosphonolipid phatidylcholine |
-
2018
- 2018-11-13 CN CN201811349079.3A patent/CN109456359A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103087091A (en) * | 2011-10-27 | 2013-05-08 | 上海秀新臣邦医药科技有限公司 | L-alpha-choline glycerophosphate synthesis method |
| CN103304594A (en) * | 2013-06-18 | 2013-09-18 | 上海科利生物医药有限公司 | Preparation method of L-alpha-glycerophosphoryl choline |
| CN104193778A (en) * | 2014-08-14 | 2014-12-10 | 苏州富士莱医药股份有限公司 | Crystallization method of liquid glycerylphosphorylcholine |
| CN104356160A (en) * | 2014-11-05 | 2015-02-18 | 合肥创新医药技术有限公司 | Purification process of L-alpha-glycerophosphoryl choline |
| CN108329344A (en) * | 2017-12-29 | 2018-07-27 | 中山百灵生物技术有限公司 | A kind of purification process of glycerophosphonolipid phatidylcholine |
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| Title |
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Application publication date: 20190312 |