CN102964377A - Method for preparing natural L-alpha-glycerol phosphatidylcholine - Google Patents
Method for preparing natural L-alpha-glycerol phosphatidylcholine Download PDFInfo
- Publication number
- CN102964377A CN102964377A CN2012105133091A CN201210513309A CN102964377A CN 102964377 A CN102964377 A CN 102964377A CN 2012105133091 A CN2012105133091 A CN 2012105133091A CN 201210513309 A CN201210513309 A CN 201210513309A CN 102964377 A CN102964377 A CN 102964377A
- Authority
- CN
- China
- Prior art keywords
- tertiary butyl
- natural
- butyl ether
- phosphatidylcholine
- methyl tertiary
- 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.)
- Granted
Links
Abstract
The invention discloses a method for preparing natural L-alpha-glyceryl phosphatide dipalmitoyl phosphatidyl choline. The method comprises the following steps of: dissolving natural lecithin having the known content of phosphatidylcholine into methyl tertiary butyl ether; filtering out undissolved substances and regulating the temperature to 5-55 DEG C; adding anhydrous low carbon alcohol and hydroxide choline into mixing liquid in a molar rate of anhydrous low carbon alcohol to phosphatidylcholine of (3:1)-(600:1)_to stir and react for 0.25-4 hours; pouring out supernate; dissolving oily precipitates with absolute ethyl alcohol and precipitating the oily precipitates by methyl tertiary butyl ether; removing the supernate after the precipitation is totally finished; repeatedly dissolving the precipitates by the absolute ethyl alcohol and precipitating the precipitates by the methyl tertiary butyl ether for 2-3 times; vacuumizing and drying obtained oily products. By the method, transesterification between the phosphatidylcholine and the anhydrous low carbon alcohol is carried out by using hydroxide choline as a catalyst and the methyl tertiary butyl ether as a solvent so as to obtain glycerol phosphatidylcholine (GPC) or natural lecithin deacylation substances using the GPC as a main part; and moreover, the method is simple in process, mild and safe in reaction conditions, and can guarantee the safety of the obtained products used as functional food addictives or medical health-care products.
Description
Technical field
The present invention relates to medicine, functional foodstuff industry and catalysis technical field, be specifically related to the preparation method of a kind of natural L-α-glyceryl phosphatide phatidylcholine.
Background technology
L-α-glyceryl phosphatide phatidylcholine (L-α-glycerophosphocholine is hereinafter to be referred as GPC) is the aqueous phospholipid of naturally occurring a kind of uniqueness in the human body.Studies show that GPC not only can improve different steps crowd's memory capability and cognitive ability, especially to the elderly, can effectively prevent and treat senile dementia, and the elderly's cerebral apoplexy phenomenon is had certain restraining effect; Simultaneously, it can also promote the release of human growth hormone, and teen-age height is made moderate progress, and also can effectively regulate middle-aged people's hormone balance, plays the effect of beauty treatment, delaying senility.Therefore, GPC can be widely used in medicine, healthcare products and functional foodstuff industry.
In recent years, some have occurred and contained the functional health product of GPC and other natural phospholipid deacylated tRNA base thing, but producer adopts the method for chemosynthesis to produce GPC mostly both at home and abroad.EP0486100 is by D-acetone glycerol and 2-oxygen-2-chloro-1, after the reaction of 3-diepoxy phosphorus pentane again with Trimethylamine 99 open loop condensation, the used raw material of this process is unstable, needs pressurized operation in the simultaneous reactions process, the condition harshness.EP0502357 then reacts D-acetone glycerol and Tosyl chloride to 18h first under 0 ° of C, obtain the acetone glycerol p-toluenesulfonic esters, again with the condensation reaction of phosphorylcholine tetramethyl ammonium, can obtain product GPC after the hydrolysis, although this method has been avoided the problem of pressurized operation, but still exist raw material unstable, the problem that complex process and cost are higher.The disclosed scheme of CN101544667A is after first Racemic glycidol being made the Racemic glycidol p-toluenesulfonic esters, prepare GPC with the condensation of phosphorylcholine tetraethyl-ammonium salt again, avoided the defective of raw material Racemic glycidol purifying difficulty, but the reaction process more complicated, total recovery is lower.The disclosed scheme of WO2007145476 is to utilize 2，3-epoxy-1-propanol and phosphorylcholine under the condition that Isopropylamine exists, and carries out nucleophilic addition and prepares GPC, obtained certain producing effects, but in the process material purity has been had relatively high expectations, and reaction yield is low.Usually, complex process, the yield by the synthetic GPC of chemical method low and used poisonous chemical raw material, its product to be used for food and there is very large potential safety hazard in medical aspect more.
From the natural matters such as soybean lecithin or Ovum Gallus domesticus Flavus lecithin through hydrolysis slough aliphatic side chains and obtain GPC be its as the more favourable preparation approach of Medicines and Health Product and functional food additives, compare with chemical method, side reaction is less, product is more natural.The disclosed scheme of US2864848 adopts water-soluble mercury salt to make catalyzer, and the phosphatide emulsion is prepared GPC in boiling Water Under solution, though raw material is natural, product yield is low, and separates poisonous mercury salt complex process.The disclosed scheme of EP0217765 and WO90/13552 all adopts sodium methylate as catalyzer, prepare GPC by the alcoholysis soybean lecithin, this process is higher to ingredient requirement, saponification reaction just can occur in the existence of a small amount of water, a large amount of organic solvents and water have been used in the product separation process simultaneously, both increase cost, caused again environmental pollution.Document [Chem.Phys.lipid.4.104 (1970)] has been reported the technique take tetrabutylammonium as catalyst for ester exchange reaction, although gentle than mercury salt, the residual edible safety that still affects product of 4-butyl ammonium.The disclosed scheme of CN102516292A is as catalyzer with low-boiling amine, by natural phospholipid reaction preparation GPC, reaction conditions is gentle, the time is short, product purity is high, and catalyzer can reclaim use together by distillation mode and methyl alcohol, simplified preparation technology, but low-boiling amine does not still possess the characteristic of totally nontoxic, and there be certain threat in a large amount of uses of methyl alcohol to the security of production process and product; There is production safety hidden danger in ether as solvent in this technique simultaneously.
Summary of the invention
For existing prepare take natural phosphatidyl choline as raw material that the catalyzer that exists in the GPC technique is poisonous, solvent ether uses dangerous, reactant methanol that there are the problems such as security hidden danger in technique and product.The present invention has proposed the preparation method of a kind of natural L-α-glyceryl phosphatide phatidylcholine on the basis of lot of experiments.This preparation method is take bursine as catalyzer, and methyl tertiary butyl ether carries out transesterification reaction as solvent by phosphatidylcholine and nontoxic low-carbon alcohol, obtains GPC or take GPC as main natural phospholipid deacylated tRNA base thing.
In order to achieve the above object, the present invention adopts following technical scheme:
The preparation method of a kind of natural L-α-glyceryl phosphatide phatidylcholine, concrete preparation process is as follows:
The natural phosphatidyl choline of known phosphatidylcholine content is dissolved in methyl tertiary butyl ether, adjusts the temperature to 5～55 ° of C behind the elimination insolubles; Under this temperature condition, be 3:1～600:1 according to anhydrous low-carbon alcohol and phosphatidylcholine mol ratio, add the pure and mild catalyzer bursine of anhydrous low-carbon, the consumption that makes bursine in the reaction system is every liter of 1～30mmol, stirring reaction 0.25～4 hour; Reaction is outwelled supernatant liquor after finishing; with oily throw out anhydrous alcohol solution; and precipitate with methyl tertiary butyl ether; the fully rear abandoning supernatant of precipitation; repeatedly precipitate 2～3 times with anhydrous alcohol solution and with methyl tertiary butyl ether again; the oily product that obtains is carried out vacuum-drying under the condition that Vanadium Pentoxide in FLAKES exists, namely obtain take the mixture of glyceryl phosphatide phatidylcholine as main natural phospholipid deacylated tRNA base thing.
Further, described anhydrous low-carbon alcohol adopts a kind of in methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol or the isopropylcarbinol.
Further, described natural phosphatidyl choline is from the extract of soybean, yolk or pluck, and wherein the content of phosphatidylcholine is 20%～98%.
The mixture of the natural phospholipid deacylated tRNA base thing that the present invention obtains comprises glyceryl phosphatide phatidylcholine (GPC), L-ALPHA-GPE (GPE) and glyceryl phosphatide acyl Serine (GPS); because three's character is similar; and have similar physiological function and health-care effect; when therefore being used as the additive of medicine, healthcare products and functional foodstuff in industry, the three can be combined together use.Simultaneously its content is relevant with raw material, when the phosphatidylcholine content in the natural Yelkin TTS is 80% when above, obtains the higher GPC of purity.Reaction principle of the present invention is as follows:
Wherein, R1 and R2 represent the aliphatic hydrocarbon of C13-C25; R3 represents
With
In a kind of, three kinds of materials that obtain are respectively GPC, GPE and GPS.
Beneficial effect of the present invention is as follows:
1, bursine is as the effective shift reaction of catalysis fatty acyl group of catalyzer, and the reaction times is short, mild condition; And can keep phosphoramide bond stability in the feed composition, thereby keep the peculiar structure of natural phospholipid.Simultaneously, choline is the common food additive, a small amount of residually also can not affect its safe handling even have in product.
2, used in the reaction process that toxicity is little, boiling point is high and used the methyl tertiary butyl ether of safety to be solvent, so that preparation process and product are more safe and reliable.
3, the methyl alcohol during preferred green dehydrated alcohol replacement classical inverse is answered has ensured further that as reactant products therefrom is used for the security of healthcare products and medicine.
Embodiment
The preparation method of natural L-α of the present invention-glyceryl phosphatide phatidylcholine, concrete preparation process is as follows:
The natural phosphatidyl choline of known phosphatidylcholine content is dissolved in methyl tertiary butyl ether, adjusts the temperature to 5～55 ° of C behind the elimination insolubles; Under this temperature condition, be 3:1～600:1 according to anhydrous low-carbon alcohol and phosphatidylcholine mol ratio, add the pure and mild catalyzer bursine of anhydrous low-carbon, the consumption that makes bursine in the reaction system is every liter of 1～30mmol, stirring reaction 0.25～4 hour; Reaction is outwelled supernatant liquor after finishing; with oily throw out anhydrous alcohol solution; and precipitate with methyl tertiary butyl ether; the fully rear abandoning supernatant of precipitation; repeatedly precipitate 2～3 times with anhydrous alcohol solution and with methyl tertiary butyl ether again; the oily product that obtains is carried out vacuum-drying under the condition that Vanadium Pentoxide in FLAKES exists, namely obtain take the mixture of glyceryl phosphatide phatidylcholine as main natural phospholipid deacylated tRNA base thing.
Even described catalyzer bursine has a small amount of residual its safe handling that also can not affect in product, its free choline is additive commonly used in the food.
Described methyl tertiary butyl ether toxicity is little, boiling point is high and use safety, and the methyl tertiary butyl ether among the present invention is available other energy dissolving lecithin and safety low-poison solvents also.
Described dehydrated alcohol also can be used a kind of the substituting in methyl alcohol, n-propyl alcohol, Virahol, propyl carbinol or the isopropylcarbinol, but preferred dehydrated alcohol.This is because dehydrated alcohol has environmental protection and the advantage such as renewable, has guaranteed that products therefrom is used for the security of healthcare products and medicine.
Described natural phosphatidyl choline is from the extract of soybean, yolk or pluck, and wherein the content of phosphatidylcholine is 20%～98%.
Catalyzer among the present invention is not only applicable to the preparation of L-α-glyceryl phosphatide phatidylcholine, also applicable to the extensive transesterification reaction such as the preparation of biofuel.The natural phospholipid deacylated tRNA base thing that simultaneously the present invention makes both can directly apply to medicine, healthcare products and functional food field, also can be used as the precursor of semi-synthetic phosphatide, for the preparation of the required synthetic phospholipid of pharmaceutical preparation.
Embodiment 1
Be that 40% soybean lecithin is dissolved in the 38mL methyl tertiary butyl ether with 5g phosphatidylcholine content, the elimination insolubles, add round-bottomed flask and place thermostat water bath to be heated to 40 ° of C, under this temperature condition, adding 1.2mL dehydrated alcohol and 0.8mL concentration is the ethanolic soln of the bursine of 0.3mol/L again, stirring reaction 2 hours.
Reaction is outwelled supernatant liquor after finishing; the oily throw out is dissolved with the 5mL anhydrous methanol; and adding 20mL methyl tertiary butyl ether precipitates; the fully rear abandoning supernatant of precipitation; repeat again 3 times with dissolve with methanol and with the operation of methyl tertiary butyl ether precipitation; at last the oily product that obtains is carried out vacuum-drying under the condition that Vanadium Pentoxide in FLAKES exists; obtaining the 1.021g outward appearance is that flaxen natural phospholipid deacylated tRNA base thing take GPC as the master (is GPC; the mixture of GPE and GPS); after testing; wherein the content of GPC accounts for 50.3% of product total mass, and yield is 76.0%.
Embodiment 2
The difference of present embodiment and embodiment 1 is, be that 60% soybean lecithin is dissolved in the 30mL methyl tertiary butyl ether with 5g phosphatidylcholine content, the elimination insolubles, add round-bottomed flask and place thermostat water bath to be heated to 50 ° of C, under this temperature condition, adding 8mL dehydrated alcohol and 2mL concentration is the ethanolic soln of the bursine of 0.3mol/L again, stirring reaction 1 hour.It is that flaxen after testing, wherein the content of GPC accounts for 73.2% of product total mass take GPC as main natural phospholipid deacylated tRNA base thing (being the mixture of GPC, GPE and GPS) that present embodiment obtains the 1.086g outward appearance, and yield is 78.4%.
Embodiment 3
The difference of present embodiment and embodiment 2 only is that phosphatidylcholine content is 95% in the soybean lecithin, and temperature of reaction is 40 ° of C, and the reaction times is 3h.After the reaction bottom oily throw out is dissolved with the 5mL anhydrous methanol, adding the 20mL methyl tertiary butyl ether precipitates again, the fully rear abandoning supernatant of precipitation, repeatedly carry out 3 times with dissolve with methanol and with the operation of methyl tertiary butyl ether precipitation, then carry out vacuum drying treatment under the condition that the product Vanadium Pentoxide in FLAKES is existed, and under the condition that diatomite exists, utilize volume ratio under 4 ° of C, to carry out crystallization for the dehydrated alcohol of 6:4 and the mixed solution of ether, obtain GPC crystal 1.026g.133 ° of C of fusing point,
(10% the aqueous solution), results of elemental analyses is: C, 37.1%; H, 7.80%; N, 5.43%.Take deuterated methanol as solvent,
1The position of main peaks: 4.36 (m, 2H) in the H NMR spectrogram, 3.91 (m, 2H), 3.82 (m, 1H), 3.61 (m, 2H), 3.58 (m, 2H), 3.27 (s, 9H).
Embodiment 4
The difference of present embodiment and embodiment 3 is, is that 90% soybean lecithin is dissolved in the 30mL methyl tertiary butyl ether with 2g phosphatidylcholine content, adds 10mL dehydrated alcohol and 0.145 bursine, 30 ° of C of temperature of reaction, stirring reaction 0.3 hour.Present embodiment obtains the intimate colourless GPC of being of 0.409g outward appearance, and purity is higher, and yield is 67.2%.
Embodiment 5
The difference of present embodiment and embodiment 2 is, be that 90% soybean lecithin is dissolved in the 25mL methyl tertiary butyl ether with 1g phosphatidylcholine content, add round-bottomed flask and place thermostat water bath to be heated to 25 ° of C, under this temperature condition, adding 11.5mL dehydrated alcohol and 3.5mL concentration is the ethanolic soln of the bursine of 0.3mol/L again, stirring reaction 4 hours.Present embodiment obtains the intimate colourless GPC of being of 0.132g outward appearance, and yield is 43.4%.
Embodiment 6
The difference of present embodiment and embodiment 5 is, be that 95% soybean lecithin is dissolved in the 25mL methyl tertiary butyl ether with 0.4g phosphatidylcholine content, regulate its temperature to 5 ° C, under this temperature condition, adding 13mL dehydrated alcohol and 2mL concentration is the ethanolic soln of the bursine of 0.3mol/L again, stirring reaction 4 hours.Present embodiment obtains the intimate colourless GPC of being of 0.0696g outward appearance, and purity is higher, and yield is 54.2%.
Embodiment 7
The difference of present embodiment and embodiment 3 is, adopts propyl carbinol to replace ethanol to react in the reaction.Present embodiment obtains the intimate colourless GPC of being of 0.832g outward appearance, and yield is 54.6%.
Claims (3)
1. the preparation method of natural L-α-glyceryl phosphatide phatidylcholine is characterized in that, concrete preparation process is as follows:
The natural phosphatidyl choline of known phosphatidylcholine content is dissolved in methyl tertiary butyl ether, adjusts the temperature to 5～55 ° of C behind the elimination insolubles; Under this temperature condition, be 10:1～600:1 according to anhydrous low-carbon alcohol and phosphatidylcholine mol ratio, add the pure and mild catalyzer bursine of anhydrous low-carbon, the consumption that makes bursine in the reaction system is every liter of 1～30mmol, stirring reaction 0.25～4 hour; Reaction is outwelled supernatant liquor after finishing; with oily throw out anhydrous alcohol solution; and precipitate with methyl tertiary butyl ether; the fully rear abandoning supernatant of precipitation; repeatedly precipitate 2～3 times with anhydrous alcohol solution and with methyl tertiary butyl ether again; the oily product that obtains is carried out vacuum-drying in the presence of Vanadium Pentoxide in FLAKES, namely obtain take the mixture of glyceryl phosphatide phatidylcholine as main natural phospholipid deacylated tRNA base thing.
2. the preparation method of natural L-α as claimed in claim 1-glyceryl phosphatide phatidylcholine is characterized in that, described anhydrous low-carbon alcohol adopts a kind of in methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol or the isopropylcarbinol.
3. the preparation method of natural L-α as claimed in claim 1-glyceryl phosphatide phatidylcholine is characterized in that, described natural phosphatidyl choline is from the extract of soybean, yolk or pluck, and wherein the content of phosphatidylcholine is 20%～98%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210513309.1A CN102964377B (en) | 2012-11-30 | 2012-11-30 | Method for preparing natural L-alpha-glycerol phosphatidylcholine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210513309.1A CN102964377B (en) | 2012-11-30 | 2012-11-30 | Method for preparing natural L-alpha-glycerol phosphatidylcholine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102964377A true CN102964377A (en) | 2013-03-13 |
| CN102964377B CN102964377B (en) | 2015-05-27 |
Family
ID=47794837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210513309.1A Expired - Fee Related CN102964377B (en) | 2012-11-30 | 2012-11-30 | Method for preparing natural L-alpha-glycerol phosphatidylcholine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102964377B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105682481A (en) * | 2013-10-21 | 2016-06-15 | 酶学技术有限公司 | Compositions comprising choline and derivatives thereof, uses thereof and processes for their preparation |
| CN108516989A (en) * | 2018-05-18 | 2018-09-11 | 榆林学院 | A kind of preparation method of phosphatide deacylation substratess |
| CN109265478A (en) * | 2018-10-30 | 2019-01-25 | 榆林学院 | A method of glycerolphosphocholine is prepared based on egg shell |
| CN109776601A (en) * | 2014-06-10 | 2019-05-21 | 凯米股份公司 | For purifying L- α-glyceryl phosphoryl choline technique |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61158990A (en) * | 1984-12-28 | 1986-07-18 | Nippon Oil & Fats Co Ltd | Production of glycerophosphorylcholine |
| JPS6216439A (en) * | 1985-07-15 | 1987-01-24 | Nippon Oil & Fats Co Ltd | Production of phosphatidylcholine |
| JPH01287091A (en) * | 1988-01-20 | 1989-11-17 | Q P Corp | Phospholipid derivative and cosmetic containing the same |
| CN101270035A (en) * | 2007-03-22 | 2008-09-24 | 石药集团中奇制药技术（石家庄）有限公司 | Novel method for synthesizing 3-benzyl group glycerol alcohol and application of the compound |
| CN101544667A (en) * | 2008-03-27 | 2009-09-30 | 南京莱尔生物化工有限公司 | Method for synthesizing L-alpha choline glycerophosphatide |
| CN102516292A (en) * | 2011-11-08 | 2012-06-27 | 西北大学 | Natural L-alpha-glycerophosphocholine (GPC) and preparation method thereof |
-
2012
- 2012-11-30 CN CN201210513309.1A patent/CN102964377B/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61158990A (en) * | 1984-12-28 | 1986-07-18 | Nippon Oil & Fats Co Ltd | Production of glycerophosphorylcholine |
| JPS6216439A (en) * | 1985-07-15 | 1987-01-24 | Nippon Oil & Fats Co Ltd | Production of phosphatidylcholine |
| JPH01287091A (en) * | 1988-01-20 | 1989-11-17 | Q P Corp | Phospholipid derivative and cosmetic containing the same |
| CN101270035A (en) * | 2007-03-22 | 2008-09-24 | 石药集团中奇制药技术（石家庄）有限公司 | Novel method for synthesizing 3-benzyl group glycerol alcohol and application of the compound |
| CN101544667A (en) * | 2008-03-27 | 2009-09-30 | 南京莱尔生物化工有限公司 | Method for synthesizing L-alpha choline glycerophosphatide |
| CN102516292A (en) * | 2011-11-08 | 2012-06-27 | 西北大学 | Natural L-alpha-glycerophosphocholine (GPC) and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 孙清瑞等: "化学催化法制备甘油磷酸胆碱的研究", 《油脂工程》 * |
| 张甜甜等: "大豆磷脂制备甘油磷脂酰胆碱均相催化反应研究", 《应用化工》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105682481A (en) * | 2013-10-21 | 2016-06-15 | 酶学技术有限公司 | Compositions comprising choline and derivatives thereof, uses thereof and processes for their preparation |
| CN109776601A (en) * | 2014-06-10 | 2019-05-21 | 凯米股份公司 | For purifying L- α-glyceryl phosphoryl choline technique |
| CN109776601B (en) * | 2014-06-10 | 2022-02-15 | 凯米股份公司 | Process for purifying L-alpha-glycerophosphorylcholine |
| CN108516989A (en) * | 2018-05-18 | 2018-09-11 | 榆林学院 | A kind of preparation method of phosphatide deacylation substratess |
| CN109265478A (en) * | 2018-10-30 | 2019-01-25 | 榆林学院 | A method of glycerolphosphocholine is prepared based on egg shell |
| CN109265478B (en) * | 2018-10-30 | 2021-07-06 | 榆林学院 | Method for preparing glycerophosphatidylcholine based on egg shells |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102964377B (en) | 2015-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102516292B (en) | Natural L-alpha-glycerophosphocholine (GPC) and preparation method thereof | |
| CN102964377B (en) | Method for preparing natural L-alpha-glycerol phosphatidylcholine | |
| CN101967160B (en) | One-step method for preparing raceme DL, D or L-a-glycerin phosphorus acyl choline | |
| CN103641858B (en) | A kind of tenofovir disoproxil fumarate and preparation method thereof | |
| CN111689878A (en) | Preparation process of trifluoromethanesulfonic anhydride | |
| CN104327114A (en) | Preparation method of phosphatidyl serine | |
| CN103087091A (en) | L-alpha-choline glycerophosphate synthesis method | |
| CA2610575C (en) | Process for the preparation and isolation of phosphatides | |
| CN104817436B (en) | Method for preparing high-purity ethylhexylglycerin | |
| CN109476687A (en) | A kind of preparation method of chiral phosphorus acid esters | |
| CN102633833B (en) | Creatine phosphate sodium preparation method | |
| KR101995642B1 (en) | Manufacturing method of food-grade choline alfocerate from phosphatidylcholine | |
| CN104086592B (en) | A kind of preparation method of fosfomycin trometamol | |
| CN108048497A (en) | A kind of method that glycerolphosphocholine is prepared using phosphatidase | |
| CN100391962C (en) | Method for synthesizing polypren phosphate | |
| CN102861532B (en) | Octadecanol glucose gemini surfactant and preparation method thereof | |
| CN102093416B (en) | Method for synthesizing sodium ibandronate | |
| CN102286559A (en) | Method for preparing lysophosphatide and prepared lysophosphatide thereof | |
| CN105296554B (en) | Combined-enzyme method prepares the preparation method of pneumatically conveying | |
| CN102757989A (en) | Process for preparing choline glycerophosphatide (GPC) with non-aqueous phase enzymatic method | |
| CN103937845B (en) | S-(+) preparation method of-naproxen acylglycerol ester prodrugs | |
| JP6265550B2 (en) | Ascorbic acid derivative composition and method for producing the same, ascorbic acid derivative solution, and external preparation for skin | |
| CN112899315B (en) | Synthesis method of stable isotope labeled 3-chloro-1, 2-propylene glycol fatty acid diester | |
| CN102976938A (en) | Method for obtaining resveratrol through Heck coupling | |
| JPH06228170A (en) | Phosphatidylchromanol derivative, its production, antioxidizing agent and emulsifying agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20150527 Termination date: 20181130 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |