CN106810574A - A kind of production method of lysophosphatidyl choline - Google Patents
A kind of production method of lysophosphatidyl choline Download PDFInfo
- Publication number
- CN106810574A CN106810574A CN201710229662.XA CN201710229662A CN106810574A CN 106810574 A CN106810574 A CN 106810574A CN 201710229662 A CN201710229662 A CN 201710229662A CN 106810574 A CN106810574 A CN 106810574A
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- CN
- China
- Prior art keywords
- choline
- glycerophosphatide
- lysophosphatidyl
- dibutyltin oxide
- oxide complex
- 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.)
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- 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 System
- 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
- C07F9/10—Phosphatides, e.g. lecithin
Abstract
A kind of production method of lysophosphatidyl choline, with choline glycerophosphatide as raw material, is acylated, you can obtain the lysophosphatidyl choline containing single ester group, low production cost through tin complexing, O.Present invention process route is short, and processing method is simple, and purifying products are easy.
Description
Technical field
Synthesize from choline glycerophosphatide the present invention relates to the synthetically produced method of lysophosphatidyl choline, more particularly to one kind
The production method of the lysophosphatidyl choline containing single ester group.
Background technology
Lysophosphatidyl choline product as obtained from phosphatid ylcholine removes a fatty acyl group.Phosphatid ylcholine（Also
Claim lecithin）, it is widely present in animal and plant body, in the brain of animal, content is more in adrenal gland and cell.Compared to phosphatidyl
Choline, the HLB values of lysophosphatidyl choline（Amphipathic property equilibrium valve）Greatly, lipophile is not only remained, also because of nonpolar base
Group reduction and make its hydrophilicity increase, its wettability, emulsibility, emulsifying capacity are superior to phosphatid ylcholine.Haemolysis phosphorus
Phosphatidylcholine plays the role of important in the institutional framework for improving baked product.Lysophosphatidyl choline also has bioactivity,
Prevention, diagnosis and treatment to atherosclerosis play the role of critically important.At present, lysophosphatidyl choline is in food, change
The aspects such as cosmetic, medicine are in an increasingly wide range of applications, so the lysophosphatidyl choline for effectively preparing high-purity just shows
Obtain most important.
The method that tradition prepares lysophosphatidyl choline is obtained through phospholipase A1, A2 hydrolytic phosphatides phatidylcholine.Day
This rich in normal times etc. has been invented the hydrolase being made up of phospholipase A1 or A2 and has acted on the hydration lecithin life as raw material
Produce lysolecithin（Japanese patent application publication No. CN1197115）.The David in the U.S. has invented and has been catalyzed phosphatide using phospholipase A2
Phatidylcholine hydrolysis in mix reagent prepares lysophosphatidyl choline（U.S. Patent Publication No. CN1210560）.Due to phosphatide
The price of enzyme is very high, and industrial production cost is higher.Further, since selected phosphatid ylcholine often contains different ester groups,
Therefore be difficult to obtain the lysophosphatidyl choline containing single ester group.
The content of the invention
The purpose of the present invention be just directed to it is above-mentioned the problems of in the prior art and provide it is a kind of it is new effectively
The method for preparing the lysophosphatidyl choline containing single ester group, the method, low production cost, accessory substance is few, hemolytic phosphatidyl
The separating-purifying of choline is easier.
The purpose of the present invention is achieved through the following technical solutions：
A kind of production method of lysophosphatidyl choline, with choline glycerophosphatide as raw material, comprises the steps：
（1）The preparation of choline glycerophosphatide-Dibutyltin oxide complex：Choline glycerophosphatide is dissolved in absolute ethyl alcohol, plus
Enter Dibutyltin oxide, be heated to reflux 0.5 ~ 2 hour, after reaction terminates, be cooled to room temperature, filter, washed with anhydrous isopropyl alcohol
Filter cake, Vacuum dry filter cake obtains white choline glycerophosphatide-Dibutyltin oxide complex；Described choline glycerophosphatide and two
The ratio of the amount of the material of butyl tin oxide is 1.0:1~1.1:1, described absolute ethyl alcohol consumption is 10 ~ 50 mls/g of glycerine phosphorus
Sour choline；
（2）The preparation of lysophosphatidyl choline crude product：Under agitation, will be through step（1）Choline glycerophosphatide-the dibutyl of gained
Tin oxide complex is placed in a kind of organic solvent, sequentially adds triethylamine, fat acyl chloride, 0.5 ~ 3 is stirred at 50 ~ 85 DEG C small
When, after reaction terminates, room temperature is cooled to, distilled water is added, stir 0.5 hour, filtrate decompression is concentrated to give lysophosphatide by filtering
Phatidylcholine crude product；Described choline glycerophosphatide-Dibutyltin oxide complex is 1 with the ratio of the amount of the material of fat acyl chloride:
1.0~1:1.1, described fat acyl chloride and the ratio of the amount of the material of triethylamine is 1:1.0~1:1.1, the use of the organic solvent
It is 100 ~ 250 mls/g of choline glycerophosphatides-Dibutyltin oxide complex to measure, and the consumption of described distilled water is 5 ~ 10 millis
Liter/gram choline glycerophosphatide-Dibutyltin oxide complex；
（3）Lysophosphatidyl choline crude product recrystallizes to obtain lysophosphatidyl choline product：By step（2）The hemolytic phosphatidyl of gained
Choline crude product obtains lysophosphatidyl choline product with acetonitrile as solvent recrystallization.
Organic solvent described in step (2) is tetrahydrofuran or 1,4- dioxane.
Fat acyl chloride described in step (2) is stearyl chloride, palmitoyl chloride or oleoyl chloride.
Acetonitrile-ethanol mixture described in step (3), acetonitrile is 100 with the volume ratio of ethanol:1~100:5.
It is an advantage of the invention that：1. the present invention is acylated, you can obtain with choline glycerophosphatide as raw material through tin complexing, O-
Lysophosphatidyl choline containing single ester group, low production cost.2. present invention process route is short, and processing method is simple, product
Purifying is easy.
Specific embodiment
It is described in further detail with reference to embodiments of the invention：
A kind of production method of lysophosphatidyl choline, with choline glycerophosphatide as raw material, comprises the steps：
（1）The preparation of choline glycerophosphatide-Dibutyltin oxide complex：Choline glycerophosphatide is dissolved in absolute ethyl alcohol, plus
Enter Dibutyltin oxide, be heated to reflux 0.5 ~ 2 hour, after reaction terminates, be cooled to room temperature, filter, washed with anhydrous isopropyl alcohol
Filter cake, Vacuum dry filter cake obtains white choline glycerophosphatide-Dibutyltin oxide complex；Described choline glycerophosphatide and two
The ratio of the amount of the material of butyl tin oxide is 1.0:1~1.1:1, described absolute ethyl alcohol consumption is 10 ~ 50 mls/g of glycerine phosphorus
Sour choline；
（2）The preparation of lysophosphatidyl choline crude product：Under agitation, will be through step（1）Choline glycerophosphatide-the dibutyl of gained
Tin oxide complex is placed in a kind of organic solvent, sequentially adds triethylamine, fat acyl chloride, 0.5 ~ 3 is stirred at 50 ~ 85 DEG C small
When, after reaction terminates, room temperature is cooled to, distilled water is added, stir 0.5 hour, filtrate decompression is concentrated to give lysophosphatide by filtering
Phatidylcholine crude product；Described choline glycerophosphatide-Dibutyltin oxide complex is 1 with the ratio of the amount of the material of fat acyl chloride:
1.0~1:1.1, described fat acyl chloride and the ratio of the amount of the material of triethylamine is 1:1.0~1:1.1, the use of the organic solvent
It is 100 ~ 250 mls/g of choline glycerophosphatides-Dibutyltin oxide complex to measure, and the consumption of described distilled water is 5 ~ 10 millis
Liter/gram choline glycerophosphatide-Dibutyltin oxide complex；
（3）Lysophosphatidyl choline crude product recrystallizes to obtain lysophosphatidyl choline product：By step（2）The hemolytic phosphatidyl of gained
Choline crude product obtains lysophosphatidyl choline product with acetonitrile as solvent recrystallization.
Organic solvent described in step (2) is tetrahydrofuran or 1,4- dioxane.
Fat acyl chloride described in step (2) is stearyl chloride, palmitoyl chloride or oleoyl chloride.
Acetonitrile-ethanol mixture described in step (3), acetonitrile is 100 with the volume ratio of ethanol:1~100:5.
Embodiment 1
Stearoyl lysolecithin（1- stearoyl-sn- glycerine -3- Phosphorylcholines）Preparation：
（1）The preparation of choline glycerophosphatide-Dibutyltin oxide complex：By 30 grams（0.11mol）Choline glycerophosphatide is dissolved in
In 500 milliliters of absolute ethyl alcohols, 24.9 grams are added（0.1mol）Dibutyltin oxide, is heated to reflux 0.5 hour, is cooled to room temperature,
Filtering, washed with anhydrous isopropyl alcohol in filter cake to filtrate without choline glycerophosphatide, Vacuum dry filter cake obtains 50.6 grams at 60 DEG C
White choline glycerophosphatide-Dibutyltin oxide complex.
（2）Under agitation, by 25.3 grams（0.05mol）Choline glycerophosphatide-Dibutyltin oxide complex is placed in 3000
In milliliter tetrahydrofuran, 6 grams are sequentially added（0.059 mol）Triethylamine, 16 grams（0.053mol）Tallow acyl chlorides, at 50 DEG C
Stirring 3 hours, after reaction terminates, is cooled to room temperature, adds 200 milliliters of distilled water, stirs 0.5 hour, filtering, by filtrate decompression
It is concentrated to give 25 grams of stearoyl lysolecithin crude products.
（3）By 25 grams of stearoyl lysolecithin crude products with volume ratio be 100:1 acetonitrile-ethanol mixture is solvent weight
Crystallization, obtains 22.5 grams of stearoyl lysolecithin products, and yield is 83.3%, and purity is 98.1%.
Claims (4)
1. a kind of production method of lysophosphatidyl choline, it is characterised in that：With choline glycerophosphatide as raw material, including following steps
Suddenly：
（1）The preparation of choline glycerophosphatide-Dibutyltin oxide complex：Choline glycerophosphatide is dissolved in absolute ethyl alcohol, plus
Enter Dibutyltin oxide, be heated to reflux 0.5 ~ 2 hour, after reaction terminates, be cooled to room temperature, filter, washed with anhydrous isopropyl alcohol
Filter cake, Vacuum dry filter cake obtains white choline glycerophosphatide-Dibutyltin oxide complex；Described choline glycerophosphatide and two
The ratio of the amount of the material of butyl tin oxide is 1.0:1~1.1:1, described absolute ethyl alcohol consumption is 10 ~ 50 mls/g of glycerine phosphorus
Sour choline；
（2）The preparation of lysophosphatidyl choline crude product：Under agitation, will be through step（1）Choline glycerophosphatide-the dibutyl of gained
Tin oxide complex is placed in a kind of organic solvent, sequentially adds triethylamine, fat acyl chloride, 0.5 ~ 3 is stirred at 50 ~ 85 DEG C small
When, after reaction terminates, room temperature is cooled to, distilled water is added, stir 0.5 hour, filtrate decompression is concentrated to give lysophosphatide by filtering
Phatidylcholine crude product；Described choline glycerophosphatide-Dibutyltin oxide complex is 1 with the ratio of the amount of the material of fat acyl chloride:
1.0~1:1.1, described fat acyl chloride and the ratio of the amount of the material of triethylamine is 1:1.0~1:1.1, the use of the organic solvent
It is 100 ~ 250 mls/g of choline glycerophosphatides-Dibutyltin oxide complex to measure, and the consumption of described distilled water is 5 ~ 10 millis
Liter/gram choline glycerophosphatide-Dibutyltin oxide complex；
（3）Lysophosphatidyl choline crude product recrystallizes to obtain lysophosphatidyl choline product：By step（2）The hemolytic phosphatidyl of gained
Choline crude product obtains lysophosphatidyl choline product with acetonitrile-ethanol mixture as solvent recrystallization.
2. according to the production method of the lysophosphatidyl choline described in claim 1, it is characterised in that：Described in step (2)
Organic solvent be tetrahydrofuran or 1,4- dioxane.
3. according to the production method of the lysophosphatidyl choline described in claim 1, it is characterised in that：Described in step (2)
Fat acyl chloride be stearyl chloride, palmitoyl chloride or oleoyl chloride.
4. according to the production method of the lysophosphatidyl choline described in claim 1, it is characterised in that：Described in step (3)
Acetonitrile-ethanol mixture, the volume ratio of acetonitrile and ethanol is 100:1~100:5.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710229662.XA CN106810574A (en) | 2017-04-10 | 2017-04-10 | A kind of production method of lysophosphatidyl choline |
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| CN201710229662.XA CN106810574A (en) | 2017-04-10 | 2017-04-10 | A kind of production method of lysophosphatidyl choline |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109096326A (en) * | 2018-10-09 | 2018-12-28 | 江苏东南纳米材料有限公司 | A kind of high-purity lysophosphatidyl choline and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1650215A1 (en) * | 2004-10-13 | 2006-04-26 | CHEMI S.p.A. | Process for preparing lysophoshatidylcholine |
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2017
- 2017-04-10 CN CN201710229662.XA patent/CN106810574A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1650215A1 (en) * | 2004-10-13 | 2006-04-26 | CHEMI S.p.A. | Process for preparing lysophoshatidylcholine |
Non-Patent Citations (1)
| Title |
|---|
| 刘杨静 等: "1-十一烯酰溶血磷脂的选择性合成与表征", 《武汉轻工大学学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109096326A (en) * | 2018-10-09 | 2018-12-28 | 江苏东南纳米材料有限公司 | A kind of high-purity lysophosphatidyl choline and preparation method thereof |
| CN109096326B (en) * | 2018-10-09 | 2021-04-30 | 江苏东南纳米材料有限公司 | High-purity lysophosphatidylcholine and preparation method thereof |
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Application publication date: 20170609 |