CN106282251A - A kind of preparation method of PHOSPHATIDYL ETHANOLAMINE - Google Patents
A kind of preparation method of PHOSPHATIDYL ETHANOLAMINE Download PDFInfo
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Abstract
The invention discloses the preparation method of a kind of PHOSPHATIDYL ETHANOLAMINE, comprise the following steps: (1) chooses crude lecithin, add ethanol solution after 70 ~ 80 DEG C of stirring extraction 5 ~ 10h, evaporated under reduced pressure solvent, concentrate must be extracted, extraction concentrate adds water stirring and emulsifying uniformly, obtain emulsion；(2) adding enzyme liquid in emulsion, described enzyme liquid is the Choline phosphatase solution containing diethanolamine hydrochloride, and regulation pH value is 6.5 ~ 7.5, and regulating temperature after mixing is 30 ~ 40 DEG C of reaction 20 ~ 30h, obtains reactant liquor；(3) in reactant liquor, add the layering of organic solvent extraction, after choosing organic phase washed with water, organic facies is concentrated in vacuo, obtain concentrate, in concentrate, add cooling recrystallization after dehydrated alcohol heating for dissolving, isolate dehydrated alcohol insoluble matter, drying to obtain PHOSPHATIDYL ETHANOLAMINE.This preparation method concise in technology, cost and energy consumption are relatively low, safety, it is easy to accomplish industrialized production.
Description
Technical field
The invention belongs to phosphatide technique, be specifically related to the preparation method of a kind of PHOSPHATIDYL ETHANOLAMINE.
Background technology
PHOSPHATIDYL ETHANOLAMINE (PE) is the phospholipids compounds that a class is important, and also known as cephalin, existing for biosphere
In phospholipid, its content is only second to phosphatidylcholine (PC), the physiological action special due to it and receive much concern, its getting up early apply
In field of food industry, along with deepening continuously of research, its function and range of application the most constantly expand, especially high-purity
PHOSPHATIDYL ETHANOLAMINE be the most gradually applied to field of pharmaceutical preparations, prepared by the emulsifying agent and the liposome that can be used as pharmaceutical preparation
Adjuvant, it may also be used for regulation mitochondrial dysfunction, treat the function such as depression and anxiety disorder.Existing report about phospholipid
Acyl ethanolamine has animals and plants to extract column chromatography, chemical synthesis and enzyme catalysis method.Animals and plants extraction method such as patent
The natural phospholipid acyl that method disclosed in CN201410841454.1, CN10038618C and CN201510395419.6 obtains
Ethanolamine content is relatively low, and consumption of organic solvent is big, and technique is loaded down with trivial details, and the amount of filler needed for purification is big, with high costs, and manually closes
Become PHOSPHATIDYL ETHANOLAMINE such as patent CN201210430649.8 and CN201010137564.1, its technique in actual production because of
Productivity is low and is difficult to, and in technique because of use phosphorus oxychloride, the noxious substance such as Phosphorous chloride. and Hydrazoic acid,sodium salt and should not examine
The advantages such as considering, enzyme process catalysis method has mild condition in addition, and technique is simple to operation and Costco Wholesale is relatively low, but research is the most not
Deep enough.
Summary of the invention
It is an object of the invention to provide the preparation method of a kind of PHOSPHATIDYL ETHANOLAMINE, this preparation method concise in technology, become
This and energy consumption are relatively low, safety, it is easy to accomplish industrialized production.
The above-mentioned purpose of the present invention is achieved through the following technical solutions: the preparation side of a kind of PHOSPHATIDYL ETHANOLAMINE
Method, comprises the following steps:
(1) crude lecithin is chosen, after addition ethanol solution stirs extraction 5 ~ 10h in 70 ~ 80 DEG C, evaporated under reduced pressure solvent, obtain extraction
Concentrate, adds water stirring and emulsifying in extraction concentrate uniformly, obtains emulsion；
(2) adding enzyme liquid in emulsion, described enzyme liquid is the Choline phosphatase solution containing diethanolamine hydrochloride, and regulation pH value is 6.5
~ 7.5, regulating temperature after mixing is 30 ~ 40 DEG C of reaction 20 ~ 30h, obtains reactant liquor；
(3) in reactant liquor, add the layering of organic solvent extraction, after choosing organic phase washed with water, organic facies is concentrated in vacuo,
Concentrate, recrystallization of lowering the temperature after adding dehydrated alcohol heating for dissolving in concentrate, isolate dehydrated alcohol insoluble matter, be dried i.e.
Obtain PHOSPHATIDYL ETHANOLAMINE.
In the preparation method of above-mentioned PHOSPHATIDYL ETHANOLAMINE:
Crude lecithin described in step (1) is preferably derived from Semen sojae atricolor or sunflower seed.
Described in step (1), in ethanol solution, the volumn concentration of ethanol is preferably 90 ~ 100%, when the volume hundred of ethanol
When point content is 100%, for dehydrated alcohol, it is 1:4 ~ 8mL with the volume ratio of crude lecithin.
Described in step (1), water is pure water, and it is preferably 1g:4 ~ 7.5 mL with extraction concentrate with magnitude relation.
Enzyme liquid and being preferably with magnitude relation of water in step (1) in step (2): 1:1 ~ 2.
Described in step (2), in enzyme liquid, the consumption of diethanolamine hydrochloride is preferably 1 ~ 3 times of crude lecithin gross mass, described phosphorus
In ESD solution, the enzyme of Choline phosphatase is lived and is preferably 5-6U/mL.
Organic solvent described in step (3) is preferably dichloromethane or hexamethylene, and it is preferred with the volume ratio of reactant liquor
It is 1 ~ 3:1.
In step (3), concentrate and dehydrated alcohol is preferably 1g:7 ~ 10mL with magnitude relation.
In step (3), heating for dissolving temperature is preferably 50 ~ 60 DEG C, and temperature during cooling recrystallization is preferably 0 ~ 10 DEG C, time
Between be preferably 5 ~ 8h.
The weight/mass percentage composition of PHOSPHATIDYL ETHANOLAMINE described in step (3) is more than 60%.
The invention have the advantages that
(1) raw material used by the present invention is crude lecithin, thus cheap；
(2) the preparation method integrated artistic of PHOSPHATIDYL ETHANOLAMINE of the present invention is succinct, mild condition, and holistic cost is relatively low, it is easy to real
Existing industrialization, prepared phosphatidylethanolamine content more than 60%, purity is higher；
(3) in the preparation method of PHOSPHATIDYL ETHANOLAMINE of the present invention, raw material first passes through simple purification in advance, then carries out subsequent enzymatic
Reaction and purification, concise in technology, energy consumption is relatively low, advantages of nontoxic raw materials, it is easy to accomplish industrialized production, to China's phospholipid industry, health care
Food and pharmaceutical industries are all by significant.
Detailed description of the invention
Embodiment 1
Further illustrate the present invention below in conjunction with specific embodiment, but the scope of protection of present invention do not limit to
Following embodiments.
Embodiment 1
By 100 milliliters of (120 grams) Crude soybean lecithin in 400 milliliters of 92%(volumn concentrations) ethanol solution 70 DEG C stirring
Extracting 5 hours, evaporated under reduced pressure alcohol extraction liquid obtains 60 grams of concentrate, adds 240 milliliters pure toward 60 grams of extract concentrate
Water purification stirring and emulsifying is uniform, is subsequently added 240 milliliters containing Choline phosphatase and the enzyme liquid of diethanolamine hydrochloride, wherein hydrochloric acid second in enzyme liquid
The quality of hydramine 120 grams, in enzyme liquid, the enzyme of Choline phosphatase is lived is 5U/mL, and regulation pH is 6.5.Mixing and emulsifying thing and enzyme liquid, in 30
DEG C reaction 20 hours.480 milliliters of hexamethylene extracting and demixing, hexamethylene layer suitable quantity of water is added after completion of the reaction in reaction system
Washing, is concentrated in vacuo organic facies and obtains hexamethylene concentrate 110 grams, and addition dehydrated alcohol 770 milliliters is in 50 DEG C of heating for dissolving, subsequently
System keeps 5 hours in 0 DEG C, isolates dehydrated alcohol insoluble matter, and vacuum drying obtains PHOSPHATIDYL ETHANOLAMINE totally 12 grams, content warp
HPLC method is determined as 61%.
Embodiment 2
By thick to 100 milliliters (110 grams) sunflower seed lecithin in 400 milliliters of volume 95%(volumn concentrations) ethanol solution 70 DEG C
Stirring extraction 5 hours, evaporated under reduced pressure alcohol extraction liquid obtains 65 grams of concentrate, adds 260 milliliters toward 65 grams of extract concentrate
Pure water stirring and emulsifying uniform, be subsequently added 130 milliliters containing Choline phosphatase and the enzyme liquid of diethanolamine hydrochloride, wherein salt in enzyme liquid
The quality 120 grams of acid ethanolamine, in enzyme liquid, the enzyme of Choline phosphatase is lived is 5U/mL, and regulation pH is 6.5.Mixing and emulsifying thing and enzyme liquid,
React 20 hours in 30 DEG C.Adding 1040 milliliters of hexamethylene extracting and demixing in reaction system after completion of the reaction, hexamethylene layer is used
Suitable quantity of water is washed, and organic facies is concentrated in vacuo and obtains hexamethylene concentrate 100 grams, adds dehydrated alcohol 700 milliliters and adds thermosol in 50 DEG C
Solving, system keeps 5 hours in 0 DEG C subsequently, isolates dehydrated alcohol insoluble matter, and vacuum drying obtains PHOSPHATIDYL ETHANOLAMINE totally 10
Gram, content is determined as 62% through HPLC method.
Embodiment 3
By 200 milliliters of (240 grams) Crude soybean lecithin in 1600 milliliter of 90% ethanol solution 80 DEG C stirring extraction 10 hours, decompression
It is evaporated alcohol extraction liquid and obtains 120 grams, add 880 milliliters of pure water stirring and emulsifying uniformly toward extract concentrate, be subsequently added
880 milliliters contain Choline phosphatase and the enzyme liquid of diethanolamine hydrochloride, wherein in enzyme liquid the quality of diethanolamine hydrochloride be raw materials quality be
720 grams, in enzyme liquid, the enzyme of Choline phosphatase is lived is 6U/mL, and regulation pH is 7.5.Mixing and emulsifying thing and enzyme liquid are little in 40 DEG C of reactions 30
Time.Adding 1760 milliliters of dichloromethane extracting and demixing in reaction system after completion of the reaction, organic facies suitable quantity of water is washed, vacuum
Concentrate organic facies and obtain dichloromethane concentrate 180 grams, add 1800 milliliters of dehydrated alcohol in 60 DEG C of heating for dissolving, subsequently system in
0 DEG C keeps 8 hours, isolates dehydrated alcohol insoluble matter, and vacuum drying obtains PHOSPHATIDYL ETHANOLAMINE 16 grams, and content is surveyed through HPLC method
It is set to 64%.
Embodiment 4
By thick to 200 milliliters (220 grams) sunflower seed lecithin in 1600 milliliter of 90% ethanol solution 80 DEG C stirring extraction 9 hours, decompression
It is evaporated alcohol extraction liquid and obtains 125 grams, add 800 milliliters of pure water stirring and emulsifying uniformly toward extract concentrate, be subsequently added
800 milliliters contain Choline phosphatase and the enzyme liquid of diethanolamine hydrochloride, wherein in enzyme liquid the quality of diethanolamine hydrochloride be raw materials quality be
600 grams, in enzyme liquid, the enzyme of Choline phosphatase is lived is 6U/mL, and regulation pH is 7.5.Mixing and emulsifying thing and enzyme liquid are little in 40 DEG C of reactions 20
Time.Adding 1600 milliliters of dichloromethane extracting and demixing in reaction system after completion of the reaction, organic facies suitable quantity of water is washed, vacuum
Concentrate organic facies and obtain dichloromethane concentrate 175 grams, add 1600 milliliters of dehydrated alcohol in 55 DEG C of heating for dissolving, subsequently system in
5 DEG C keep 7 hours, isolate dehydrated alcohol insoluble matter, and vacuum drying obtains PHOSPHATIDYL ETHANOLAMINE 15 grams, and content is surveyed through HPLC method
It is set to 63%.
Embodiment 5
By 100 milliliters of (120 grams) Crude soybean lecithin in 600 milliliters of volume 100% ethanol solution 75 DEG C stirring extraction 8 hours, subtract
Pressure is evaporated ethanol solution extract and obtains 60 grams of concentrate, and past 60 grams of extract concentrate add the pure water stirring of 240 milliliters
Emulsifying is uniform, is subsequently added 240 milliliters containing Choline phosphatase and the enzyme liquid of diethanolamine hydrochloride, the wherein matter of diethanolamine hydrochloride in enzyme liquid
Measuring 120 grams, in enzyme liquid, the enzyme of Choline phosphatase is lived is 5.5U/mL, and regulation pH is 7.0.Mixing and emulsifying thing and enzyme liquid, in 35 DEG C of reactions
25 hours.Adding 960 milliliters of hexamethylene extracting and demixing in reaction system after completion of the reaction, hexamethylene layer suitable quantity of water is washed,
Organic facies is concentrated in vacuo and obtains hexamethylene concentrate 100 grams, add dehydrated alcohol 800 milliliters in 55 DEG C of heating for dissolving, subsequently systems
Keeping 6 hours in 10 DEG C, isolate dehydrated alcohol insoluble matter, vacuum drying obtains PHOSPHATIDYL ETHANOLAMINE totally 10 grams, content warp
HPLC method is determined as 65%.
A part of specific embodiment is enumerated above, and the present invention will be described, it is necessary to it is pointed out here that be upper and lower specific embodiment
It is served only for that the present invention is further illustrated, does not represent limiting the scope of the invention.Other people make according to the present invention
The nonessential amendment of some gone out and adjustment still fall within protection scope of the present invention.
Claims (10)
1. a preparation method for PHOSPHATIDYL ETHANOLAMINE, is characterized in that comprising the following steps:
(1) crude lecithin is chosen, after addition ethanol solution stirs extraction 5 ~ 10h in 70 ~ 80 DEG C, evaporated under reduced pressure solvent, obtain extraction
Concentrate, adds water stirring and emulsifying in extraction concentrate uniformly, obtains emulsion；
(2) adding enzyme liquid in emulsion, described enzyme liquid is the Choline phosphatase solution containing diethanolamine hydrochloride, and regulation pH value is 6.5
~ 7.5, regulating temperature after mixing is 30 ~ 40 DEG C of reaction 20 ~ 30h, obtains reactant liquor；
(3) in reactant liquor, add the layering of organic solvent extraction, after choosing organic phase washed with water, organic facies is concentrated in vacuo,
Concentrate, recrystallization of lowering the temperature after adding dehydrated alcohol heating for dissolving in concentrate, isolate dehydrated alcohol insoluble matter, be dried i.e.
Obtain PHOSPHATIDYL ETHANOLAMINE.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: the thick ovum described in step (1)
Phospholipid sources is in Semen sojae atricolor or sunflower seed.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: described in step (1), ethanol is molten
In liquid, the volumn concentration of ethanol is 90 ~ 100%, and it is 1:4 ~ 8mL with the volume ratio of crude lecithin.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: described in step (1), water is pure
Water purification, it is 1g:4 ~ 7.5mL with extraction concentrate with magnitude relation.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: step (2) enzyme liquid and step (1)
Middle water with magnitude relation be: 1:1 ~ 2.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: described in step (2) in enzyme liquid
The consumption of diethanolamine hydrochloride is 1 ~ 3 times of crude lecithin gross mass, and in described Choline phosphatase solution, the enzyme work of Choline phosphatase is 5 ~ 6U/
mL。
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: organic described in step (3)
Solvent is dichloromethane or hexamethylene, and it is 1 ~ 3:1 with the volume ratio of reactant liquor.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: concentrate and nothing in step (3)
Water-ethanol is 1g:7 ~ 10mL with magnitude relation.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: heating for dissolving temperature in step (3)
Degree is 50 ~ 60 DEG C, and temperature during cooling recrystallization is 0 ~ 10 DEG C, and the time is 5 ~ 8h.
The preparation method of PHOSPHATIDYL ETHANOLAMINE the most according to claim 1, is characterized in that: phosphatidyl described in step (3)
The weight/mass percentage composition of ethanolamine is more than 60%.
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| CN201610651533.5A CN106282251A (en) | 2016-08-11 | 2016-08-11 | A kind of preparation method of PHOSPHATIDYL ETHANOLAMINE |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438508A (en) * | 2018-10-29 | 2019-03-08 | 翁源广业清怡食品科技有限公司 | A kind of preparation method of phosphatidyl-ethanolamine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003091263A1 (en) * | 2002-04-25 | 2003-11-06 | Doosan Corporation | Method for producing phosphatidylethanolamine and lysophosphatidylethanolamine using non-organic solvent system |
| CN105420301A (en) * | 2015-11-13 | 2016-03-23 | 广东省食品工业研究所 | Preparation method of phosphatidic acid |
-
2016
- 2016-08-11 CN CN201610651533.5A patent/CN106282251A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003091263A1 (en) * | 2002-04-25 | 2003-11-06 | Doosan Corporation | Method for producing phosphatidylethanolamine and lysophosphatidylethanolamine using non-organic solvent system |
| CN105420301A (en) * | 2015-11-13 | 2016-03-23 | 广东省食品工业研究所 | Preparation method of phosphatidic acid |
Non-Patent Citations (1)
| Title |
|---|
| LEKH RAJ JUNEJA ET AL: "Kinetic evaluation of conversion of phosphatidylcholine to phosphatidylethanolamine by phospholipase D from different sources", 《BIOCHIMICA ET BIOPHYSICA ACTA》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438508A (en) * | 2018-10-29 | 2019-03-08 | 翁源广业清怡食品科技有限公司 | A kind of preparation method of phosphatidyl-ethanolamine |
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Address after: 512627 Shaoguan, Wengyuan Weng Weng Weng Town Industrial Park Applicant after: Wengyuan Guangye Qingyi Food Technology Co., Ltd. Applicant after: Guangdong Food Industry Research Institute Co Ltd Address before: 512627 Shaoguan, Wengyuan Weng Weng Weng Town Industrial Park Applicant before: Wengyuan Guangye Qingyi Food Technology Co., Ltd. Applicant before: Guangdong Prov. Food Industry Inst. |
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Application publication date: 20170104 |