CN1733776A - High purity yolk cephalin preparation method - Google Patents
High purity yolk cephalin preparation method Download PDFInfo
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- CN1733776A CN1733776A CN 200510050676 CN200510050676A CN1733776A CN 1733776 A CN1733776 A CN 1733776A CN 200510050676 CN200510050676 CN 200510050676 CN 200510050676 A CN200510050676 A CN 200510050676A CN 1733776 A CN1733776 A CN 1733776A
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- cephalin
- preparation
- yolk
- mixed solvent
- methylene dichloride
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- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 210000002969 egg yolk Anatomy 0.000 title claims abstract description 21
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 title claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 142
- 239000012046 mixed solvent Substances 0.000 claims abstract description 29
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000741 silica gel Substances 0.000 claims abstract description 18
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 18
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000005238 degreasing Methods 0.000 claims abstract description 10
- 239000012065 filter cake Substances 0.000 claims abstract description 10
- 238000004108 freeze drying Methods 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- 238000004809 thin layer chromatography Methods 0.000 claims description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 9
- 238000003828 vacuum filtration Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 5
- 238000002161 passivation Methods 0.000 claims description 4
- 230000008929 regeneration Effects 0.000 claims description 3
- 238000011069 regeneration method Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 1
- 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 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 229940067606 lecithin Drugs 0.000 abstract 1
- 235000010445 lecithin Nutrition 0.000 abstract 1
- 239000000787 lecithin Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 238000011010 flushing procedure Methods 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 229960001866 silicon dioxide Drugs 0.000 description 13
- 230000002262 irrigation Effects 0.000 description 7
- 238000003973 irrigation Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 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
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Abstract
The invention discloses a preparation method for yolk cephalin with high purity, which comprises following steps: 1) degreasing to the fresh yolk with acetone, filtering in vacuum, extracting the filter cake; combining the filter liquid to condense for coarse phospholipid; 2) filling purified silica gel pole by wet way with dichloromethane-carbinol mixed liquid, clearing with dichloromethane-carbinol solvent; 3) dissolving the coarse phospholipid with dichloromethane- carbinol liquid, adding chromatography pole, and collecting the flow liquid; 4) when the lecithin begins to penetrate, using carbinol to clear, and collecting the flow liquid; 5) analyzing the flow liquid with TLC to combine cephalin distillate, condensing in vacuum, freeze drying to obtain cephalin with purity more than 90%; 6) using carbinol with ammonia to regenerate pole, clearing with dichloromethane-carbino mixed solvent for new sample. This invention is convenient to operate, and fit to industrial production in large scale.
Description
Technical field
The present invention relates to phospholipid, relate in particular to a kind of preparation method of high purity yolk cephalin.
Background technology
Phosphatide is a class phosphorated lipid material, is mainly derived from soybean and yolk.Phosphatidylethanolamine (Phosphatidyl Ethanolamine, be called for short PE) and phosphatidylcholine (Phosphatidyl Choline, be called for short PC) be two kinds of important phosphatide wherein, be commonly called as kephalin and Yelkin TTS, be widely used in industries such as food, medicine, makeup.The high purity kephalin is good natural surface active agent, have unique biological activity and physiological function, nontoxic, pollution-free, non-stimulated, readily biodegradable and be subjected to the great attention of domestic and international scientific and technological circle and industry member, its demand is increasing year by year, but at present purity is greater than kephalin product China of 90% dependence on import still, therefore develops to be fit to China's national situation, low-cost, high purity kephalin preparation method, has important economy and social value.
The process for purification of kephalin mainly contains extraction process, column chromatography, the precipitator method, membrane separation process etc.Column chromatography because have easy and simple to handle, good separating effect, do not need expensive device, advantage such as treatment capacity is big, thereby receive much attention.In column chromatography research, mainly concentrate on inexpensive silica gel and aluminum oxide at present.For aluminum oxide normally PC go out the peak earlier, and for silica gel normally PE go out the peak earlier.In order to obtain highly purified PE, this patent adopts silica gel as sorbent material, selects for use the less yolk of except that PC and PE other phosphatide as raw material simultaneously.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of high purity yolk cephalin.
The step of method is as follows:
1) fresh yolk is used the acetone degreasing earlier, vacuum filtration, and the filter cake alcoholic extraction, merging filtrate, vacuum concentration obtains raw phospholipid;
2) adorn post through the silica gel of passivation with methylene chloride-methanol mixed solvent wet method, earlier with the flushing of methylene chloride-methanol mixed solvent;
3) raw phospholipid adds chromatography column with methylene chloride-methanol mixed solvent dissolving back, and begins to collect effluent liquid;
4) treat that Yelkin TTS begins to penetrate the pure washed with methanol in back, collects effluent liquid;
5) effluent liquid is analyzed back merging kephalin fraction through thin-layer chromatography TLC, can obtain purity greater than 90% kephalin after vacuum concentration, freeze-drying;
6) at last with the methanol solution regeneration pillar that contains ammoniacal liquor, again with sample introduction again after the flushing of methylene chloride-methanol mixed solvent.
Of the present invention having the following advantages:
1) technology is simple, and is easy to operate, is suitable for the heavy industrialization preparation;
2) silica gel can be recycled, and cost is lower;
3) the silica gel column chromatography process can at room temperature be carried out;
4) product purity height can get purity greater than 90% kephalin product after this technology is refining;
5) for the high yield of egg in recent years, drug on the market, the solution that is difficult to problems such as depositing provides novel method, for a new road is opened up in the deep processing of egg, promotes the development of birds, beasts and eggs industry.
Embodiment
The raw phospholipid that solvent-extraction process obtains, with at room temperature crossing silicagel column after the dissolving of methylene chloride-methanol mixed solvent, treat to use pure washed with methanol instead after PC begins to flow out, collect effluent liquid, analyze the fraction that the back merges kephalin through TLC, after concentrated, lyophilize, can get the kephalin product again.Methanol solution regeneration, the methylene chloride-methanol mixed solvent of pillar through containing ammoniacal liquor can be recycled after washing.
Embodiment 1
Fresh yolk is earlier with acetone degreasing three times, and vacuum filtration, filter cake be with 95% alcoholic extraction secondary, merging filtrate, and vacuum concentration obtains raw phospholipid.Analyze through HPLC, contain PC75.0% (wt%), PE16.0% (wt%) in the raw phospholipid.Get water content and be 10% silica gel with the methylene dichloride mixed solvent wet method dress 1/2 inch ID * 20 centimetre pillar of Ф (column volume is 25ml) that contains methyl alcohol 10%, earlier with the methylene dichloride mixed solvent flushing 50ml that contains methyl alcohol 10%.Advancing 60ml concentration is the raw phospholipid solution (solvent is the dichloromethane solution that contains methyl alcohol 10%) of 100mg/ml, then uses the 200ml washed with methanol, and flow rate control begins to collect effluent liquid (collecting by every part of about 5ml) at 0.4ml/min behind the application of sample.Effluent liquid merges the kephalin fraction after TLC analyzes, get kephalin 0.55g after vacuum concentration, freeze-drying, and the content of kephalin is 91% in the HPLC analysed preparation.Pillar is with the methanol solution that contains ammonia 2% (weight percent) (is the preparation of 25% ammoniacal liquor by containing weight percent) flushing 150ml, with sample introduction again behind the methylene dichloride mixed solvent flushing 100ml that contains methyl alcohol 10%, same irrigation flow rate is controlled at 0.4ml/min again.
Embodiment 2
Fresh yolk is earlier with acetone degreasing three times, and vacuum filtration, filter cake be with 95% alcoholic extraction secondary, merging filtrate, and vacuum concentration obtains raw phospholipid.Analyze through HPLC, contain PC75.0% (wt%), PE16.0% (wt%) in the raw phospholipid.Get water content and be 12% silica gel with the methylene dichloride mixed solvent wet method dress 1/2 inch ID * 20 centimetre pillar of Ф (column volume is 25ml) that contains methyl alcohol 20%, earlier with the methylene dichloride mixed solvent flushing 50ml that contains methyl alcohol 20%.Advancing 55ml concentration is the raw phospholipid solution (solvent is the dichloromethane solution that contains methyl alcohol 20%) of 100mg/ml, then uses the 200ml washed with methanol, and flow rate control begins to collect effluent liquid (collecting by every part of about 5ml) at 0.4ml/min behind the application of sample.Effluent liquid merges the kephalin fraction after TLC analyzes, get kephalin 0.50g after vacuum concentration, freeze-drying, and the content of kephalin is 92% in the HPLC analysed preparation.Pillar is with the methanol solution that contains ammonia 1% (weight percent) (is the preparation of 25% ammoniacal liquor by containing weight percent) flushing 200ml, with sample introduction again behind the methylene dichloride mixed solvent flushing 100ml that contains methyl alcohol 20%, same irrigation flow rate is controlled at 0.4ml/min again.
Embodiment 3
Fresh yolk is earlier with acetone degreasing secondary, and vacuum filtration, filter cake be with 95% alcoholic extraction secondary, merging filtrate, and vacuum concentration obtains raw phospholipid.Analyze through HPLC, contain PC74.0% (wt%), PE15.0% (wt%) in the raw phospholipid.Get water content and be 14% silica gel with the methylene dichloride mixed solvent wet method dress 1/2 inch ID * 20 centimetre pillar of Ф (column volume is 25ml) that contains methyl alcohol 30%, earlier with the methylene dichloride mixed solvent flushing 50ml that contains methyl alcohol 30%.Advancing 50ml concentration is the raw phospholipid solution (solvent is the dichloromethane solution that contains methyl alcohol 30%) of 100mg/ml, then uses the 200ml washed with methanol, and flow rate control begins to collect effluent liquid (collecting by every part of about 5ml) at 0.4ml/min behind the application of sample.Effluent liquid merges the kephalin fraction after TLC analyzes, get kephalin 0.46g after vacuum concentration, freeze-drying, and the content of kephalin is 90% in the HPLC analysed preparation.Pillar is with the methanol solution that contains ammonia 0.5% (weight percent) (is the preparation of 25% ammoniacal liquor by containing weight percent) flushing 300ml, with sample introduction again behind the methylene dichloride mixed solvent flushing 100ml that contains methyl alcohol 20%, same irrigation flow rate is controlled at 0.4ml/min again.
Embodiment 4
Fresh yolk is earlier with acetone degreasing secondary, and vacuum filtration, filter cake be with 95% alcoholic extraction secondary, merging filtrate, and vacuum concentration obtains raw phospholipid.Analyze through HPLC, contain PC74.0% (wt%), PE15.0% (wt%) in the raw phospholipid.Get water content and be 8% silica gel with the methylene dichloride mixed solvent wet method dress 1/2 inch ID * 20 centimetre pillar of Ф (column volume is 25ml) that contains methyl alcohol 40%, earlier with the methylene dichloride mixed solvent flushing 50ml that contains methyl alcohol 40%.Advancing 50ml concentration is the raw phospholipid solution (solvent is the dichloromethane solution that contains methyl alcohol 40%) of 100mg/ml, then uses the 200ml washed with methanol, and flow rate control begins to collect effluent liquid (collecting by every part of about 5ml) at 0.4ml/min behind the application of sample.Effluent liquid merges the kephalin fraction after TLC analyzes, get kephalin 0.43g after vacuum concentration, freeze-drying, and the content of kephalin is 90% in the HPLC analysed preparation.Pillar is with the methanol solution that contains ammonia 3% (weight percent) (is the preparation of 25% ammoniacal liquor by containing weight percent) flushing 150ml, with sample introduction again behind the methylene dichloride mixed solvent flushing 100ml that contains methyl alcohol 40%, same irrigation flow rate is controlled at 0.4ml/min again.
Embodiment 5
Fresh yolk is earlier with acetone degreasing three times, and vacuum filtration, filter cake be with 95% alcoholic extraction three times, merging filtrate, and vacuum concentration obtains raw phospholipid.Analyze through HPLC, contain PC74.5% (wt%), PE15.5% (wt%) in the raw phospholipid.Get water content and be 10% silica gel with the methylene dichloride mixed solvent wet method dress 1/2 inch ID * 20 centimetre pillar of Ф (column volume is 25ml) that contains methyl alcohol 50%, earlier with the methylene dichloride mixed solvent flushing 50ml that contains methyl alcohol 50%.Advancing 50ml concentration is the raw phospholipid solution (solvent is the dichloromethane solution that contains methyl alcohol 50%) of 100mg/ml, then uses the 200ml washed with methanol, and flow rate control begins to collect effluent liquid (collecting by every part of about 5ml) at 0.4ml/min behind the application of sample.Effluent liquid merges the kephalin fraction after TLC analyzes, get kephalin 0.40g after vacuum concentration, freeze-drying, and the content of kephalin is 89% in the HPLC analysed preparation.Pillar is with the methanol solution that contains ammonia 0.1% (weight percent) (is the preparation of 25% ammoniacal liquor by containing weight percent) flushing 500ml, with sample introduction again behind the methylene dichloride mixed solvent flushing 100ml that contains methyl alcohol 50%, same irrigation flow rate is controlled at 0.4ml/min again.
Embodiment 6
Fresh yolk is earlier with acetone degreasing three times, and vacuum filtration, filter cake be with 95% alcoholic extraction three times, merging filtrate, and vacuum concentration obtains raw phospholipid.Analyze through HPLC, contain PC74.5% (wt%), PE15.5% (wt%) in the raw phospholipid.Get water content and be 12% silica gel with containing absolute dichloromethane solvent wet method dress 1/2 inch ID * 20 centimetre pillar of Ф (column volume is 25ml), earlier with absolute dichloromethane solvent washing 50ml.Advancing 70ml concentration is the raw phospholipid solution (solvent is an absolute dichloromethane) of 100mg/ml, then uses the 200ml washed with methanol, and flow rate control begins to collect effluent liquid (collecting by every part of about 5ml) at 0.4ml/min behind the application of sample.Effluent liquid merges the kephalin fraction after TLC analyzes, get kephalin 0.65g after vacuum concentration, freeze-drying, and the content of kephalin is 91% in the HPLC analysed preparation.Pillar is with the methanol solution that contains ammonia 0.5% (weight percent) (is the preparation of 25% ammoniacal liquor by containing weight percent) flushing 200ml, uses behind the absolute dichloromethane solvent washing 100ml sample introduction again again, and same irrigation flow rate is controlled at 0.4ml/min.
Embodiment 7
Fresh yolk is used acetone degreasing three times earlier, vacuum filtration, and filter cake extracts secondary with raw spirit, merging filtrate, vacuum concentration obtains raw phospholipid.Analyze through HPLC, contain PC76.0% (wt%), PE16.5% (wt%) in the raw phospholipid.Get water content and be 12% silica gel with the methylene dichloride mixed solvent wet method dress 1/2 inch ID * 20 centimetre pillar of Ф (column volume is 25ml) that contains methyl alcohol 5%, earlier with the methylene dichloride mixed solvent flushing 50ml that contains methyl alcohol 5%.Advancing 65ml concentration is the raw phospholipid solution (solvent is the dichloromethane solution that contains methyl alcohol 30%) of 100mg/ml, then uses the 200ml washed with methanol, and flow rate control begins to collect effluent liquid (collecting by every part of about 5ml) at 0.4ml/min behind the application of sample.Effluent liquid merges the kephalin fraction after TLC analyzes, get kephalin 0.62g after vacuum concentration, freeze-drying, and the content of kephalin is 92% in the HPLC analysed preparation.Pillar is with the methanol solution that contains ammonia 1% (weight percent) (is the preparation of 25% ammoniacal liquor by containing weight percent) flushing 200ml, with sample introduction again behind the methylene dichloride mixed solvent flushing 100ml that contains methyl alcohol 5%, same irrigation flow rate is controlled at 0.4ml/min again.
Claims (4)
1. the preparation method of a high purity yolk cephalin is characterized in that, the step of method is as follows:
1) fresh yolk is used the acetone degreasing earlier, vacuum filtration, and the filter cake alcoholic extraction, merging filtrate, vacuum concentration obtains raw phospholipid;
2) adorn post through the silica gel of passivation with methylene dichloride-methanol mixed solvent wet method, earlier with methylene dichloride-methanol mixed solvent washing;
3) raw phospholipid adds chromatography column after with methylene dichloride-methanol mixed dissolution with solvents, and begins to collect effluent liquid;
4) treat that Yelkin TTS begins to penetrate the pure washed with methanol in back, collects effluent liquid;
5) effluent liquid is analyzed back merging kephalin fraction through thin-layer chromatography TLC, can obtain purity greater than 90% kephalin after vacuum concentration, freeze-drying;
6), use behind methylene dichloride-methanol mixed solvent washing sample introduction again more at last with the methanol solution regeneration pillar that contains ammoniacal liquor.
2. the preparation method of a kind of high purity yolk cephalin according to claim 1, the content that it is characterized in that methyl alcohol in said methylene dichloride-methanol mixed solvent is volume percent 0%～50%.
3. the preparation method of a kind of high purity yolk cephalin according to claim 1 is characterized in that said silica gel through passivation is meant that the silica gel water content after passivation is weight percentage 8%～14% by adding less water to reduce the activity of silica gel.
4, the preparation method of a kind of high purity yolk cephalin according to claim 1 is characterized in that the content of ammonia in the said methanol solution that contains ammoniacal liquor is weight percentage 0.1～3%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100506762A CN1321123C (en) | 2005-07-12 | 2005-07-12 | High purity yolk cephalin preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100506762A CN1321123C (en) | 2005-07-12 | 2005-07-12 | High purity yolk cephalin preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1733776A true CN1733776A (en) | 2006-02-15 |
| CN1321123C CN1321123C (en) | 2007-06-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB2005100506762A Expired - Fee Related CN1321123C (en) | 2005-07-12 | 2005-07-12 | High purity yolk cephalin preparation method |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104356161A (en) * | 2014-11-06 | 2015-02-18 | 江南大学 | Preparation method of phosphatidylcholine dilinolenate |
| CN105520120A (en) * | 2015-12-05 | 2016-04-27 | 中盐榆林盐化有限公司 | Lecithin edible salt and preparation method thereof |
| CN109096327A (en) * | 2018-08-27 | 2018-12-28 | 大连工业大学 | A kind of preparation method of high-purity yolk phospholipid acyl ethanol amine |
| CN115043872A (en) * | 2022-06-17 | 2022-09-13 | 哈尔滨工业大学 | Method for extracting deer blood phospholipid and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1279047C (en) * | 2004-10-29 | 2006-10-11 | 浙江大学 | Mixed bed ion exchange resin method for purifying lecithin and cephalin |
-
2005
- 2005-07-12 CN CNB2005100506762A patent/CN1321123C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104356161A (en) * | 2014-11-06 | 2015-02-18 | 江南大学 | Preparation method of phosphatidylcholine dilinolenate |
| CN105520120A (en) * | 2015-12-05 | 2016-04-27 | 中盐榆林盐化有限公司 | Lecithin edible salt and preparation method thereof |
| CN109096327A (en) * | 2018-08-27 | 2018-12-28 | 大连工业大学 | A kind of preparation method of high-purity yolk phospholipid acyl ethanol amine |
| CN115043872A (en) * | 2022-06-17 | 2022-09-13 | 哈尔滨工业大学 | Method for extracting deer blood phospholipid and application thereof |
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| Publication number | Publication date |
|---|---|
| CN1321123C (en) | 2007-06-13 |
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