CN102277237A - Preparation method of high-purity glyceride type fish oil - Google Patents
Preparation method of high-purity glyceride type fish oil Download PDFInfo
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- CN102277237A CN102277237A CN 201110165890 CN201110165890A CN102277237A CN 102277237 A CN102277237 A CN 102277237A CN 201110165890 CN201110165890 CN 201110165890 CN 201110165890 A CN201110165890 A CN 201110165890A CN 102277237 A CN102277237 A CN 102277237A
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- 235000021323 fish oil Nutrition 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 125000005456 glyceride group Chemical group 0.000 title abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 14
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 14
- 239000012044 organic layer Substances 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010791 quenching Methods 0.000 claims abstract description 8
- 230000000171 quenching effect Effects 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 27
- 125000004494 ethyl ester group Chemical group 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 235000019198 oils Nutrition 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000010813 municipal solid waste Substances 0.000 claims description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 15
- DVSZKTAMJJTWFG-UHFFFAOYSA-N docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(O)=O DVSZKTAMJJTWFG-UHFFFAOYSA-N 0.000 abstract description 13
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 239000003208 petroleum Substances 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000000034 method Methods 0.000 description 15
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 12
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000007812 deficiency Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 2
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses a preparation method of high-purity glyceride type fish oil, comprising the following steps: (1) taking 650-800g of glyceride type fish oil and 110-180g of alkali at weight ratio, dissolving alkali in 0.4-1.6L of water, evenly mixing in a reactor, and adding the glyceride type fish oil; (2) introducing nitrogen into the reactor until material is completely reacted; (3) cooling materials in the reactor to be below 25DEG C; (4) extracting by petroleum ether or n-hexane to obtain free polyunsaturated fatty acid; (5) adding the free polyunsaturated fatty acid into the reactor; (6) adding zinc powder into the reactor; (7) immediately pouring reaction liquid into crushed ice for quenching reaction; and (8) extracting a crude product subjected to quenching reaction by the petroleum ether or n-hexane, and washing an organic layer with saturated salt water to obtain the glyceride type fish oil. The preparation method disclosed by the invention has the advantages of short preparation time and low manufacture cost, the prepared glyceride type fish oil keeps high content of EPA (Eicosapntemacnioc Acid) and DHA (Docosahexaenic Acid) and also has high content of triglyceride.
Description
Technical field
The present invention relates to the fish oil manufacture method, is a kind of preparation method of high purity glyceryl ester type fish oil.
Background technology
Fish oil includes timnodonic acid (EPA) and docosahexenoic acid (DHA) physiologically active ingredient, is widely used in the raw material of medicine, healthcare products.Fish oil in the market is divided into ethyl ester type fish oil and glyceryl ester type fish oil.In recent years studies show that, because ethyl ester type fish oil is at the quantitative ethanol of the mid-swap-in of esterification process, caused the lipid acid imbalance, edible back has side effects to human body, and the specific absorption after ethyl ester fish oil is oral is lower, therefore, it is feedstock production glyceryl ester type fish oil that this area was adopted ethyl ester type fish oil in recent years, to solve the deficiency of ethyl ester type fish oil.Yet there are deficiencies such as production cost height, production cycle length and content of triglyceride are lower in these methods.For example: disclosed method among the CN101348807A, though, the EPA in the glyceryl ester type fish oil and the content of DHA triglyceride level are more than 90%, but its core technology is to set up formerly to pass through C-18 reversed phase chromatography material column chromatography repeatedly, and online again mass spectrum and high performance liquid phase detect stream part and prepare purity on the basis of high-purity EPA more than 90% and DHA raw material.The deficiency of this method is: cost is high, and medicine and chemical field can't adopt this method industrialization to produce glyceryl ester type fish oil.Disclosed method among the CN101161819A, though manufacturing cost is not high, though the content of EPA and DHA at 50-80%, the content of triglyceride level is lower than 40%.The deficiency of these methods causes glyceryl ester type fish oil higher as the price of medicine and healthcare products raw material, and purity is lower, and this problem is not resolved for a long time in this area always, has limited the range of application of glyceryl ester type fish oil.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of high purity glyceryl ester type fish oil, make its produce the time short, cost of manufacture is low, has not only kept the content of high EPA and DHA in the glyceryl ester type fish oil of producing, and the content height of triglyceride level.
The present invention is achieved through the following technical solutions for achieving the above object: a kind of preparation method of high purity glyceryl ester type fish oil may further comprise the steps:
1. get ethyl ester type fish oil 650-800g, alkali 110-180g by weight, the alkali of 110-180g is dissolved in the 0.4-1.6L water, inserts in the reactor, at room temperature 0.4-1.8L ethanol is added in the reactor simultaneously, mixes, and adds ethyl ester type fish oil;
2. inflated with nitrogen in reactor is heated to 60-80 ℃ with material under nitrogen protection, reacts 1-2 hour, and is complete to material reaction;
3. the temperature of charge in the reactor is reduced to below 25 ℃, adding an amount of diluted acid adjust pH then is 2-4 again;
4. with sherwood oil or normal hexane 200-300ml * 3 extractions, the saturated NaCl solution of organic layer 300ml * 3 washings, again with sal epsom or anhydrous sodium sulfate drying 1-2 hour, remove under reduced pressure behind the solvent the free polyunsaturated fatty acid of 550-640g;
5. the free polyunsaturated fatty acid of 550-640g is inserted in the reactor, add 51-72.8g glycerine, mix the back and under nitrogen protection, be heated with stirring to 180-225 ℃;
6. get the 0.38-2.88g zinc powder and evenly be divided into 3 parts, divide to add for 3 times in the reactor, from the first time add zinc powder to time of stopped reaction be 1.5-3 hour;
7. with behind the stopped reaction, heat reaction solution pour the reaction of quenching in the trash ice immediately into;
8. the reacted crude product that quenches extracts with sherwood oil or normal hexane 100-150ml * 3, organic layer adopts saturated brine 200-300ml * 3 washings, with sal epsom or anhydrous sodium sulfate drying 1-2 hour, filters then again, filtrate decompression concentrates, and obtains 600-670g glyceryl ester type fish oil.
The timed interval that step adds zinc powders described in 6. for three times is 10-20 minute.
The present invention adopts zinc powder catalytic esterification legal system to get glyceryl ester type fish oil, and its is distinguished and existing enzyme catalysis method, and has avoided the deficiency of enzyme catalysis method.In the method for the present invention, reaction time of esterification only is 1.5-3 hour, urge significantly shortening in method 12-48 hour than common enzyme, thereby it is with short production cycle, significantly reduced production cost, be specially adapted to the suitability for industrialized production of medicine and health products trade, can make with glyceryl ester type fish oil is that the medicine and the healthcare products price of raw material significantly reduces.Glyceryl ester type fish oil purity height with the inventive method manufacturing, the total content of EPA and DHA is higher than 70%(in triglyceride level in the glyceryl ester type fish oil, that is: EPA and DHA triglyceride level are higher than 45%), content of triglyceride is higher than 60%, meets the standard-required of British Pharmacopoeia (version in 2010).
Embodiment
Example 1: it is raw material that preparation method of the present invention adopts the ethyl ester type fish oil of suitability for industrialized production, and preparation high purity glyceryl ester type fish oil contains EPA46% in the ethyl ester type fish oil, contains DHA27%, and preparation method's step is as follows:
1. get ethyl ester type fish oil 650g, alkali 180g by weight, the alkali of 180g is dissolved in the 1.6L water, inserts in the reactor, at room temperature 0.4L ethanol is added in the reactor simultaneously, mixes, and adds ethyl ester type fish oil;
2. inflated with nitrogen in reactor is heated to 70 ℃ with material under nitrogen protection, reacts 1 hour, and is complete to material reaction;
3. again the temperature of charge in the reactor is reduced to 5 ℃, adding 2N hydrochloric acid adjust pH then is 2;
4. use sherwood oil 250ml * 3 extraction, organic layer adopts saturated NaCl solution 300ml * 3 washings, uses dried over mgso again 1 hour, remove under reduced pressure behind the solvent the free polyunsaturated fatty acid of 575g;
5. the free polyunsaturated fatty acid of 575g is inserted in the reactor, add 57.5g glycerine, mix the back and under nitrogen protection, be heated with stirring to 210 ℃;
6. get the 1.15g zinc powder and evenly be divided into three parts, divide to add for three times in the reactor, be 15 minutes per pitch time that adds zinc powder for twice, from the first time add zinc powder to time of stopped reaction be 1.5 hours;
7. with behind the stopped reaction, heat reaction solution pour the reaction of quenching in the trash ice immediately into;
8. the reacted crude product that quenches extracts with sherwood oil 150ml * 3, and organic layer adopts saturated brine 200ml * 3 washings, uses dried over mgso again 1 hour, filters then, and filtrate decompression concentrates, and obtains 620g glyceryl ester type fish oil.Detect through HPL, wherein content of triglyceride is 78%, and diglyceride content is 15%, and monoglyceride content is 9%.Through gas chromatographic analysis, EPA content is 47% in the product, and the content of DHA is 25%.
Example 2: it is raw material that preparation method of the present invention adopts the ethyl ester type fish oil of suitability for industrialized production, and preparation high purity glyceryl ester type fish oil contains EPA50% in the ethyl ester type fish oil, contains DHA25%, and preparation method's step is as follows:
1. get ethyl ester type fish oil 650g, alkali 110g by weight, the alkali of 110g is dissolved in the 0.4L water, inserts in the reactor, at room temperature 1.6L ethanol is added in the reactor simultaneously, mixes, and adds ethyl ester type fish oil;
2. inflated with nitrogen in reactor is heated to 80 ℃ with material under nitrogen protection, reacts 1.5 hours, and is complete to material reaction;
3. again the temperature of charge in the reactor is reduced to 18 ℃, adding an amount of diluted acid adjust pH then is 3;
4. use normal hexane 200ml * 3 extraction, organic layer adopts saturated NaCl solution 300ml * 3 washings, uses anhydrous sodium sulfate drying again 2 hours, remove under reduced pressure behind the solvent the free polyunsaturated fatty acid of 550g;
5. the free polyunsaturated fatty acid of 550g is inserted in the reactor, add 72.8g glycerine, mix the back and under nitrogen protection, be heated with stirring to 180 ℃;
6. get the 0.38g zinc powder and evenly be divided into three parts, divide to add for three times in the reactor, be 10 minutes per pitch time that adds zinc powder for twice, from the first time add zinc powder to time of stopped reaction be 2.5 hours;
7. with behind the stopped reaction, heat reaction solution pour the reaction of quenching in the trash ice immediately into;
8. the reacted crude product that quenches extracts with normal hexane 100ml * 3, and organic layer adopts saturated brine 300ml * 3 washings, uses anhydrous sodium sulfate drying again 1.5 hours, filters then, and filtrate decompression concentrates, and obtains 600g glyceryl ester type fish oil.Detect through HPL, wherein content of triglyceride is 65%, and diglyceride content is 24%, and monoglyceride content is 12%.Through gas chromatographic analysis, EPA content is 54% in the product, and the content of DHA is 26%.
Example 3: it is raw material that preparation method of the present invention adopts the ethyl ester type fish oil of suitability for industrialized production, and preparation high purity glyceryl ester type fish oil contains EPA62% in the ethyl ester type fish oil, contains DHA21%, and preparation method's step is as follows:
1. get ethyl ester type fish oil 800g, alkali 160g by weight, the alkali of 160g is dissolved in the 1.0L water, inserts in the reactor, at room temperature 1L ethanol is added in the reactor simultaneously, mixes, and adds ethyl ester type fish oil;
2. inflated with nitrogen in reactor is heated to 60 ℃ with material under nitrogen protection, reacts 2 hours, and is complete to material reaction;
3. again the temperature of charge in the reactor is reduced to 25 ℃, adding 2N hydrochloric acid adjust pH then is 4;
4. use sherwood oil 200ml * 3 extraction, organic layer adopts saturated NaCl solution 300ml * 3 washings, uses dried over mgso again 1.5 hours, remove under reduced pressure behind the solvent the free polyunsaturated fatty acid of 640g;
5. the free polyunsaturated fatty acid of 640g is inserted in the reactor, add 51g glycerine, mix the back and under nitrogen protection, be heated with stirring to 220 ℃;
6. get the 2.88g zinc powder and evenly be divided into three parts, divide to add for three times in the reactor, be 20 minutes per pitch time that adds zinc powder for twice, from the first time add zinc powder to time of stopped reaction be 3 hours;
7. with behind the stopped reaction, heat reaction solution pour the reaction of quenching in the trash ice immediately into;
8. the reacted crude product that quenches extracts with sherwood oil 100ml * 3, and organic layer adopts saturated brine 200ml * 3 washings, uses dried over mgso again 2 hours, filters then, and filtrate decompression concentrates, and obtains 670g glyceryl ester type fish oil.Detect through HPL, wherein content of triglyceride is 67%, and diglyceride content is 21%, and monoglyceride content is 11%.Through gas chromatographic analysis, EPA content is 60% in the product, and the content of DHA is 19%.
Example 4: it is raw material that preparation method of the present invention adopts the ethyl ester type fish oil of suitability for industrialized production, and preparation high purity glyceryl ester type fish oil contains EPA62% in the ethyl ester type fish oil, contains DHA21%, and preparation method's step is as follows:
1. get ethyl ester type fish oil 750g, alkali 140g by weight, the alkali of 140g is dissolved in the 1.0L water, inserts in the reactor, at room temperature 0.8L ethanol is added in the reactor simultaneously, mixes, and adds ethyl ester type fish oil;
2. inflated with nitrogen in reactor with 650 ℃ of material heating, reacted 2 hours under nitrogen protection, and is complete to material reaction;
3. again the temperature of charge in the reactor is reduced to 25 ℃, adding 2N hydrochloric acid adjust pH then is 2;
4. use sherwood oil 300ml * 3 extraction, organic layer adopts saturated NaCl solution 300ml * 3 washings, uses dried over mgso again 80 minutes, remove under reduced pressure behind the solvent the free polyunsaturated fatty acid of 620g;
5. the free polyunsaturated fatty acid of 620g is inserted in the reactor, add 60g glycerine, mix the back and under nitrogen protection, be heated with stirring to 225 ℃;
6. get the 2.7g zinc powder and evenly be divided into 3 parts, divide to add for 3 times in the reactor, be 15 minutes per pitch time that adds zinc powder for twice, from the first time add zinc powder to time of stopped reaction be 2 hours;
7. with behind the stopped reaction, heat reaction solution pour the reaction of quenching in the trash ice immediately into;
8. the reacted crude product that quenches extracts with normal hexane 100ml * 3, and organic layer adopts saturated brine 200ml * 3 washings, uses dried over mgso again 120 minutes, filters then, and filtrate decompression concentrates, and obtains 650g glyceryl ester type fish oil.Detect through HPL, wherein content of triglyceride is 73%, and diglyceride content is 17%, and monoglyceride content is 11%.Through gas chromatographic analysis, EPA content is 61% in the product, and the content of DHA is 18%.
The timed interval that adds zinc powders described in the step 6 for three times is to be preferred version in 10-20 minute.
The equipment that uses in the method for the invention is known equipment.The inventive method not detailed description is a known technology.
Claims (2)
1. the preparation method of a high purity glyceryl ester type fish oil is characterized in that: may further comprise the steps:
1. get ethyl ester type fish oil 650-800g, alkali 110-180g by weight, the alkali of 110-180g is dissolved in the 0.4-1.6L water, inserts in the reactor, at room temperature 0.4-1.8L ethanol is added in the reactor simultaneously, mixes, and adds ethyl ester type fish oil;
2. inflated with nitrogen in reactor is heated to 60-80 ℃ with material under nitrogen protection, reacts 1-2 hour, and is complete to material reaction;
3. the temperature of charge in the reactor is reduced to below 25 ℃, adding an amount of diluted acid adjust pH then is 2-4 again;
4. with sherwood oil or normal hexane 200-300ml * 3 extractions, the saturated NaCl solution of organic layer 300ml * 3 washings, again with sal epsom or anhydrous sodium sulfate drying 1-2 hour, remove under reduced pressure behind the solvent the free polyunsaturated fatty acid of 550-640g;
5. the free polyunsaturated fatty acid of 550-640g is inserted in the reactor, add 51-72.8g glycerine, mix the back and under nitrogen protection, be heated with stirring to 180-225 ℃;
6. get the 0.38-2.88g zinc powder and evenly be divided into 3 parts, divide to add for 3 times in the reactor, from the first time add zinc powder to time of stopped reaction be 1.5-3 hour;
7. with behind the stopped reaction, heat reaction solution pour the reaction of quenching in the trash ice immediately into;
8. the reacted crude product that quenches extracts with sherwood oil or normal hexane 100-150ml * 3, organic layer adopts saturated brine 200-300ml * 3 washings, with sal epsom or anhydrous sodium sulfate drying 1-2 hour, filters then again, filtrate decompression concentrates, and obtains 600-670g glyceryl ester type fish oil.
2. the preparation method of a kind of high purity glyceryl ester type fish oil according to claim 1 is characterized in that: the timed interval that step adds zinc powders described in 6. for three times is 10-20 minute.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103242969A (en) * | 2013-05-24 | 2013-08-14 | 四川欣美加生物医药有限公司 | Preparation method of triglyceride type fish oil and prepared triglyceride type fish oil |
| CN103396303A (en) * | 2013-07-25 | 2013-11-20 | 浙江大学 | Method for separating and purifying eicosapentaenoic acid and docosahexaenoic acid from micro-algal oil or fish oil |
| CN104136008A (en) * | 2012-02-29 | 2014-11-05 | 贝朗医疗有限公司 | Hormone containing emulsion |
| WO2016058284A1 (en) * | 2014-10-13 | 2016-04-21 | 浙江医药股份有限公司新昌制药厂 | Method for preparing glyceride type polyunsaturated fatty acids |
| TWI651098B (en) * | 2012-02-29 | 2019-02-21 | Ｂ 柏藍麥桑根公司 | Hormone containing emulsion |
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|---|---|---|---|---|
| CN104136008A (en) * | 2012-02-29 | 2014-11-05 | 贝朗医疗有限公司 | Hormone containing emulsion |
| TWI651098B (en) * | 2012-02-29 | 2019-02-21 | Ｂ 柏藍麥桑根公司 | Hormone containing emulsion |
| CN110251463A (en) * | 2012-02-29 | 2019-09-20 | 贝朗医疗有限公司 | Lotion containing hormone |
| CN103242969A (en) * | 2013-05-24 | 2013-08-14 | 四川欣美加生物医药有限公司 | Preparation method of triglyceride type fish oil and prepared triglyceride type fish oil |
| CN103242969B (en) * | 2013-05-24 | 2014-11-19 | 四川欣美加生物医药有限公司 | Preparation method of triglyceride type fish oil and prepared triglyceride type fish oil |
| CN103396303A (en) * | 2013-07-25 | 2013-11-20 | 浙江大学 | Method for separating and purifying eicosapentaenoic acid and docosahexaenoic acid from micro-algal oil or fish oil |
| CN103396303B (en) * | 2013-07-25 | 2014-12-17 | 浙江大学 | Method for separating and purifying eicosapentaenoic acid and docosahexaenoic acid from micro-algal oil or fish oil |
| WO2016058284A1 (en) * | 2014-10-13 | 2016-04-21 | 浙江医药股份有限公司新昌制药厂 | Method for preparing glyceride type polyunsaturated fatty acids |
| US10030212B2 (en) | 2014-10-13 | 2018-07-24 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Method for preparing glyceride type polyunsaturated fatty acids |
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