CN108997411A - The purification process of glycerolphosphocholine - Google Patents
The purification process of glycerolphosphocholine Download PDFInfo
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- CN108997411A CN108997411A CN201810794584.2A CN201810794584A CN108997411A CN 108997411 A CN108997411 A CN 108997411A CN 201810794584 A CN201810794584 A CN 201810794584A CN 108997411 A CN108997411 A CN 108997411A
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- Prior art keywords
- mixed liquor
- glycerolphosphocholine
- temperature
- under conditions
- crystal
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- 238000000746 purification Methods 0.000 title claims abstract description 33
- 239000013078 crystal Substances 0.000 claims abstract description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000004090 dissolution Methods 0.000 claims abstract description 16
- 235000019441 ethanol Nutrition 0.000 claims abstract description 14
- 238000001704 evaporation Methods 0.000 claims abstract description 14
- 239000000287 crude extract Substances 0.000 claims abstract description 13
- 230000008020 evaporation Effects 0.000 claims abstract description 11
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004411 aluminium Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 6
- 239000010408 film Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000003930 cognitive ability Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 210000000232 gallbladder Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 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 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000007087 memory ability Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000002994 raw material 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 discloses a kind of purification process of glycerolphosphocholine, wherein the purification process includes: that mixed liquor M1 1) is made in glycerolphosphocholine crude extract and ethyl alcohol mixed dissolution；2) mixed liquor M1 is placed under conditions of temperature is 5~15 DEG C and is filtered, mixed liquor M2 is made；3) mixed liquor M2 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain a crystal N1；4) by a crystal N1 and ether mixed dissolution, mixed liquor M3 is made；5) by mixed liquor M3 peroxidating aluminium column, mixed liquor M4 is obtained；6) mixed liquor M4 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain secondary crystal N2；7) secondary crystal N2 is concentrated by evaporation, glycerolphosphocholine after purification is made.It realizes without introducing a large amount of solvents, and purification effect is more preferable, so that the higher effect of the purity of glycerolphosphocholine after purification.
Description
Technical field
The present invention relates to the finishing passes of glycerolphosphocholine, and in particular, to the purifying of glycerolphosphocholine
Method.
Background technique
Glycerolphosphocholine is the product by generating after two fatty acid chain hydrolysis on phospholipid molecule, is lecithin in human body
The catabolite of rouge.It plays particularly important effect in the synthesis and metabolism of phosphatide, for human body cognitive ability
Raising, maintenance of hormone level etc. have particularly important meaning.The study found that it is for reducing hyperlipidemia, improving always
Year man memory and cognitive ability, treatment alzheimer's disease etc. have certain effect.
Glycerophosphatide is prepared generally by modes such as chemical synthesis, chemical hydrolysis or biological enzyme hydrolysis in the prior art
Phatidylcholine, so that wherein often containing certain impurity, the purity of glycerolphosphocholine obtained also tends to lower.
Therefore it provides it is a kind of without introducing a large amount of solvents, and purification effect is more preferable, so that glycerophosphatide acyl gallbladder after purification
The problem of purification process of the higher glycerolphosphocholine of the purity of alkali is urgent need to resolve of the present invention.
Summary of the invention
For the above-mentioned prior art, the purpose of the present invention is to provide one kind without introducing a large amount of solvents, and purification effect
More preferably, so that the purification process of the higher glycerolphosphocholine of the purity of glycerolphosphocholine after purification.
To achieve the goals above, the present invention provides a kind of purification process of glycerolphosphocholine, wherein described pure
Change method includes:
1) by glycerolphosphocholine crude extract and ethyl alcohol mixed dissolution, mixed liquor M1 is made；
2) mixed liquor M1 is placed under conditions of temperature is 5~15 DEG C and is filtered, mixed liquor M2 is made；
3) mixed liquor M2 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain a crystal N1；
4) by a crystal N1 and ether mixed dissolution, mixed liquor M3 is made；
5) by mixed liquor M3 peroxidating aluminium column, mixed liquor M4 is obtained；
6) mixed liquor M4 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain secondary crystal N2；
7) secondary crystal N2 is concentrated by evaporation, glycerolphosphocholine after purification is made.
Preferably, in step 1), relative to the glycerolphosphocholine crude extract of 10g, the dosage of the ethyl alcohol is
20-40mL。
Preferably, in step 1), mixed dissolution process is to be placed under conditions of temperature is 60-80 DEG C to be stirred, and stir
Mixing rate is 300-500r/min, mixing time 10-20min.
Preferably, in step 2), filter process is that filter opening is used to be filtered for 0.2-0.5 μm of organic film.
Preferably, in step 4), relative to a crystal N1 of 10g, the dosage of the ether is 20-30mL.
Preferably, in step 4), mixed dissolution process is to be placed under conditions of temperature is 40-50 DEG C to be stirred, and stir
Mixing rate is 100-200r/min, mixing time 10-15min.
Preferably, in step 7), evaporating concentration process is to be placed in thin film evaporator to be evaporated concentration.
Through the above technical solutions, oily phosphatidyl choline crude extract is dissolved in ethyl alcohol by the present invention, then at certain temperature
Under the conditions of filter, then crystallized, obtain a crystal, further by an above-mentioned dissolution of crystals in ether, then
Secondary crystallization is carried out again after flowing through alumina column, and obtained crystal is further concentrated by evaporation.By the above-mentioned means, only introducing ethyl alcohol
And ether, even if there is slight residual, to human toxicity also very little, and this mode can obtain the higher glycerophosphatide acyl gallbladder of purity
Alkali complies with the demand of actual use.
Other features and advantages of the present invention will the following detailed description will be given in the detailed implementation section.
Specific embodiment
Detailed description of the preferred embodiments below.It should be understood that described herein specific
Embodiment is merely to illustrate and explain the present invention, and is not intended to restrict the invention.
The endpoint of disclosed range and any value are not limited to the accurate range or value herein, these ranges or
Value should be understood as comprising the value close to these ranges or value.For numberical range, between the endpoint value of each range, respectively
It can be combined with each other between the endpoint value of a range and individual point value, and individually between point value and obtain one or more
New numberical range, these numberical ranges should be considered as specific open herein.
The present invention provides a kind of purification process of glycerolphosphocholine, wherein the purification process includes:
1) by glycerolphosphocholine crude extract and ethyl alcohol mixed dissolution, mixed liquor M1 is made；
2) mixed liquor M1 is placed under conditions of temperature is 5~15 DEG C and is filtered, mixed liquor M2 is made；
3) mixed liquor M2 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain a crystal N1；
4) by a crystal N1 and ether mixed dissolution, mixed liquor M3 is made；
5) by mixed liquor M3 peroxidating aluminium column, mixed liquor M4 is obtained；
6) mixed liquor M4 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain secondary crystal N2；
7) secondary crystal N2 is concentrated by evaporation, glycerolphosphocholine after purification is made.
Oily phosphatidyl choline crude extract is dissolved in ethyl alcohol by the present invention, is filtered under the conditions of certain temperature, and laggard
Row crystallization, obtains a crystal, further by an above-mentioned dissolution of crystals in ether, then flow through after alumina column again into
Row secondary crystallization, obtained crystal are further concentrated by evaporation.By the above-mentioned means, ethyl alcohol and ether are only introduced, even if having slight
Residual, to human toxicity also very little, and this mode can obtain the higher glycerolphosphocholine of purity, and complying with actually makes
Demand.
The dosage of above-mentioned raw materials can select in a wide range, for example, in a kind of preferred embodiment of the invention
In, in step 1), relative to the glycerolphosphocholine crude extract of 10g, the dosage of the ethyl alcohol is 20-40mL.
In further preferred embodiment, in step 1), mixed dissolution process is the condition for being placed in temperature and being 60-80 DEG C
Under be stirred, and stirring rate be 300-500r/min, mixing time 10-20min.
In a kind of more preferably embodiment, in step 2), filter process is use filter opening for 0.2-0.5 μm organic
Film is filtered.
In another preferred embodiment of the invention, in step 4), relative to a crystal N1 of 10g, the second
The dosage of ether is 20-30mL.
In further preferred embodiment, in step 4), mixed dissolution process is the condition for being placed in temperature and being 40-50 DEG C
Under be stirred, and stirring rate be 100-200r/min, mixing time 10-15min.
In one kind more preferably embodiment, in step 7), evaporating concentration process is to be placed in thin film evaporator to carry out
It is concentrated by evaporation.
The present invention will be described in detail by way of examples below.Wherein, the purity of glycerolphosphocholine crude extract
It is 63.6%.
Embodiment 1
1) 10g glycerolphosphocholine crude extract and 20mL ethyl alcohol are placed under conditions of temperature is 60 DEG C with 300r/min
Stirring rate be stirred 10min, be made mixed liquor M1；
2) mixed liquor M1 is placed in the organic membrane filter under conditions of temperature is 5 DEG C through 0.3 μm, mixed liquor M2 is made；
3) mixed liquor M2 is placed under conditions of temperature is -5 DEG C and places 40h, obtain a crystal N1；
4) crystal N1 of 10g and 20mL ether are placed under conditions of temperature is 40 DEG C with the stirring rate of 100r/min
It is stirred 10min, mixed liquor M3 is made；
5) by mixed liquor M3 peroxidating aluminium column, mixed liquor M4 is obtained；
6) mixed liquor M4 is placed under conditions of temperature is -5 DEG C and places 40h, obtain secondary crystal N2；
7) secondary crystal N2 is placed in thin film evaporator and is concentrated by evaporation, glycerolphosphocholine A1 after purification is made.
(purity of glycerolphosphocholine A1 obtained is 96.5%)
Embodiment 2
1) 10g glycerolphosphocholine crude extract and 40mL ethyl alcohol are placed under conditions of temperature is 80 DEG C with 500r/min
Stirring rate be stirred 20min, be made mixed liquor M1；
2) mixed liquor M1 is placed in the organic membrane filter under conditions of temperature is 15 DEG C through 0.3 μm, mixed liquor M2 is made；
3) mixed liquor M2 is placed under conditions of temperature is 0 DEG C and places 60h, obtain a crystal N1；
4) crystal N1 of 10g and 30mL ether are placed under conditions of temperature is 50 DEG C with the stirring rate of 200r/min
It is stirred 15min, mixed liquor M3 is made；
5) by mixed liquor M3 peroxidating aluminium column, mixed liquor M4 is obtained；
6) mixed liquor M4 is placed under conditions of temperature is 0 DEG C and places 60h, obtain secondary crystal N2；
7) secondary crystal N2 is placed in thin film evaporator and is concentrated by evaporation, glycerolphosphocholine A2 after purification is made.
(purity of glycerolphosphocholine A2 obtained is 96.8%)
Embodiment 3
1) 10g glycerolphosphocholine crude extract and 30mL ethyl alcohol are placed under conditions of temperature is 70 DEG C with 400r/min
Stirring rate be stirred 15min, be made mixed liquor M1；
2) mixed liquor M1 is placed in the organic membrane filter under conditions of temperature is 10 DEG C through 0.3 μm, mixed liquor M2 is made；
3) mixed liquor M2 is placed under conditions of temperature is -3 DEG C and places 50h, obtain a crystal N1；
4) crystal N1 of 10g and 25mL ether are placed under conditions of temperature is 45 DEG C with the stirring rate of 150r/min
It is stirred 12min, mixed liquor M3 is made；
5) by mixed liquor M3 peroxidating aluminium column, mixed liquor M4 is obtained；
6) mixed liquor M4 is placed under conditions of temperature is -3 DEG C and places 50h, obtain secondary crystal N2；
7) secondary crystal N2 is placed in thin film evaporator and is concentrated by evaporation, glycerolphosphocholine A3 after purification is made.
(purity of glycerolphosphocholine A3 obtained is 97.2%)
Embodiment 4
It is operated according to the method for embodiment 1, unlike, room temperature environment is placed in (i.e. in step 1) and step 4)
20-25 DEG C) under operated, glycerolphosphocholine A4 after purification is made.(the purity of glycerolphosphocholine A4 obtained
For 89.5%)
Comparative example 1
It is operated according to the method for embodiment 1, unlike, without step 2) and step 3), it is made after purification
Glycerolphosphocholine D1.(purity of glycerolphosphocholine D1 obtained is 77.3%)
Comparative example 2
It is operated according to the method for embodiment 2, unlike, without step 3) and step 4), it is made after purification
Glycerolphosphocholine D2.(purity of glycerolphosphocholine D2 obtained is 78.9%)
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above
Detail within the scope of the technical concept of the present invention can be with various simple variants of the technical solution of the present invention are made, this
A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case where shield, can be combined in any appropriate way, in order to avoid unnecessary repetition, the present invention to it is various can
No further explanation will be given for the combination of energy.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should also be regarded as the disclosure of the present invention.
Claims (7)
1. a kind of purification process of glycerolphosphocholine, which is characterized in that the purification process includes:
1) by glycerolphosphocholine crude extract and ethyl alcohol mixed dissolution, mixed liquor M1 is made；
2) mixed liquor M1 is placed under conditions of temperature is 5~15 DEG C and is filtered, mixed liquor M2 is made；
3) mixed liquor M2 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain a crystal N1；
4) by a crystal N1 and ether mixed dissolution, mixed liquor M3 is made；
5) by mixed liquor M3 peroxidating aluminium column, mixed liquor M4 is obtained；
6) mixed liquor M4 is placed under conditions of temperature is -5~0 DEG C and places 40-60h, obtain secondary crystal N2；
7) secondary crystal N2 is concentrated by evaporation, glycerolphosphocholine after purification is made.
2. purification process according to claim 1, wherein the glycerolphosphocholine in step 1), relative to 10g
Crude extract, the dosage of the ethyl alcohol are 20-40mL.
3. purification process according to claim 1 or 2, wherein in step 1), mixed dissolution process is to be placed in temperature to be
It is stirred under conditions of 60-80 DEG C, and stirring rate is 300-500r/min, mixing time 10-20min.
4. purification process according to claim 1 or 2, wherein in step 2), filter process is to use filter opening for 0.2-
0.5 μm of organic film is filtered.
5. purification process according to claim 1 or 2, wherein described relative to a crystal N1 of 10g in step 4)
The dosage of ether is 20-30mL.
6. purification process according to claim 1 or 2, wherein in step 4), mixed dissolution process is to be placed in temperature to be
It is stirred under conditions of 40-50 DEG C, and stirring rate is 100-200r/min, mixing time 10-15min.
7. purification process according to claim 1 or 2, wherein in step 7), evaporating concentration process is to be placed in thin film evaporation
Concentration is evaporated in device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810794584.2A CN108997411A (en) | 2018-07-19 | 2018-07-19 | The purification process of glycerolphosphocholine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810794584.2A CN108997411A (en) | 2018-07-19 | 2018-07-19 | The purification process of glycerolphosphocholine |
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| Publication Number | Publication Date |
|---|---|
| CN108997411A true CN108997411A (en) | 2018-12-14 |
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ID=64600444
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810794584.2A Pending CN108997411A (en) | 2018-07-19 | 2018-07-19 | The purification process of glycerolphosphocholine |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102260286A (en) * | 2011-05-27 | 2011-11-30 | 合肥工业大学 | Method for separating and purifying crude product L-alpha-glycerophosphocholine |
| CN105017307A (en) * | 2015-07-22 | 2015-11-04 | 沈阳天峰生物制药有限公司 | Method for preparing high-purity natural L-alpha-glycerylphosphorylcholine |
| CN106083916A (en) * | 2016-06-08 | 2016-11-09 | 芜湖福民生物药业有限公司 | The preparation method of choline alfoscerate crystal |
-
2018
- 2018-07-19 CN CN201810794584.2A patent/CN108997411A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102260286A (en) * | 2011-05-27 | 2011-11-30 | 合肥工业大学 | Method for separating and purifying crude product L-alpha-glycerophosphocholine |
| CN105017307A (en) * | 2015-07-22 | 2015-11-04 | 沈阳天峰生物制药有限公司 | Method for preparing high-purity natural L-alpha-glycerylphosphorylcholine |
| CN106083916A (en) * | 2016-06-08 | 2016-11-09 | 芜湖福民生物药业有限公司 | The preparation method of choline alfoscerate crystal |
Non-Patent Citations (2)
| Title |
|---|
| 康世宗等: "L-a-甘油磷脂酰胆碱的制备、纯化及检测研究进展", 《中国油脂》 * |
| 赵成磊等: "甘油磷酸胆碱的结晶、结构解析及年产100吨原料药工艺设计", 《中国优秀硕士论文全文数据库 工程科技I辑》 * |
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