CN101161819A - Method for preparing n-3PUFA ocean glycerin ester by enzymatical process - Google Patents
Method for preparing n-3PUFA ocean glycerin ester by enzymatical process Download PDFInfo
- Publication number
- CN101161819A CN101161819A CNA2007100308629A CN200710030862A CN101161819A CN 101161819 A CN101161819 A CN 101161819A CN A2007100308629 A CNA2007100308629 A CN A2007100308629A CN 200710030862 A CN200710030862 A CN 200710030862A CN 101161819 A CN101161819 A CN 101161819A
- Authority
- CN
- China
- Prior art keywords
- 3pufa
- ocean
- glyceryl ester
- normal hexane
- remove
- 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.)
- Pending
Links
Landscapes
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
A method for preparing n-3PUFA marine glyceride through adopting enzyme method includes following steps: refined fish oil is made into n-3PUFA condensate through saponification, acidification and urea adduct method; lipase catalyzes the synthesis reaction between n-3PUFA and glycerol; n-3PUFA marine glyceride is extracted and separated; moreover, n-3PUFA is effectively concentrated in glyceride to be made into functional products which can prevent and cure cardiovascular diseases and nourish the brain and improve intelligence. The raw material of the invention, n-3PUFA, is extracted from natural fish oil, thereby being safe and effective; during production, nitrogen protection is adopted without adding synthetic antioxidant, thereby effectively preventing oxidation of n-3PUFA; with scientific and reasonable technique, the invention completes synthesis by means of biological enzyme method along with high esterification degree of reaction, higher utilization rate of raw material and easily controlled reaction process; therefore, the invention has wide market prospect.
Description
Technical field
The present invention relates to a kind of method of utilizing lipase-catalyzed synthetic n-3PUFA ocean glyceryl ester, belong to biotechnology and functional health field.
Background technology
In the present invention, " n-3PUFA " is meant the n-3 polyunsaturated fatty acid; " DHA " is meant docosahexenoic acid, and " EPA " is meant timnodonic acid.DHA in the natural fish oil and EPA mainly exist with the form of triglyceride level, and its relative content is lower, and health care and medical effect are poor, are difficult to satisfy human consumer's needs.For health care and the medical effect that improves DHA and EPA, numerous investigators are converted into corresponding ethyl ester or free form with the DHA in the glyceryl ester and EPA transesterificationization or hydrolysis, and then improve the content of DHA and EPA by various physics or chemical process, strengthen health care and the medical effect of DHA and EPA with this.Nineteen ninety U.S. FDA the researchist by a large amount of experiments after, find that glyceryl ester type, ethyl ester type and the free-fat acid type of DHA and EPA digested and assimilated variant in human body.The result of researchs such as Ikuo also shows, not only digestion and specific absorption are difficult in human body for DHA and EPA ethyl ester type, and may have potential safety hazard; Though the DHA and the EPA of free type are easy to by human consumption and absorption, oxidation generates harmful material easily, and has tart flavour, mouthfeel bad, directly is difficult to be accepted by people as eating; The glyceryl ester type of DHA and EPA not only stable in properties, be difficult for oxidation, mouthfeel good, easily absorbed by human consumption, and be the natural existence form of DHA and EPA, so the glyceryl ester type of EPA and DHA is the best product pattern of healthcare products and medicine.Moreover along with the raising of people's living standard, the human consumer is low no longer satisfied to EPA and DHA content in the natural fish oil glyceryl ester type healthcare products, and expectation provides security good and EPA and the high glyceryl ester type healthcare products of DHA content.Therefore EPA and DHA glyceride product will be the main developing direction of following fish oil healthcare products and medicine.
N-3 PUFA ocean glyceryl ester can extract acquisition from marine organisms (as tuna, sardines, cod etc.), but the content of n-3 PUFA is lower; N-3 PUFA ocean glyceryl ester also can utilize the synthetic method to obtain.British Pharmacopoeia version in 2000 and European Pharmacopoeia are defined as follows n-3 PUFA ocean glyceryl ester: n-3PUFA ocean glyceryl ester is the mixture of n-3 PUFA and the glycerine monoesters, diester and three esters that generate, wherein is mainly three esters.It is by the n-3 PUFA of high density and glycerine esterification and get.N-3 PUFA mainly contains following several: punicic acid, therapic acid, eicosatetraenoic acid (AA), timnodonic acid (EPA), 21 carbon 5 alkene acids, clupanodonic acid (DPA) and docosahexenoic acid (DHA).They are mainly derived from deep sea fish oil.The pharmacopeia regulation: the total concn of n-3 PUFA must not be less than 60% in triglyceride level, and wherein the total concn sum of DHA, EPA must not be less than 45% in glyceryl ester.N-3 PUFA ocean glyceride product is a weak yellow liquid, and is water-soluble hardly, is soluble in acetone and heptane, is slightly soluble in ethanol.Because n-3PUFA is rich in unsaturated fatty acids, therefore very easily oxidation should preserve in the container of sealing, and lucifuge is deposited under the rare gas element, and vitamin-E and tea-polyphenol etc. can be used as antioxidant and adds.N-3 PUFA ocean glyceryl ester is easily absorbed by human consumption, the interior unsaturated fatty acids of body is increased, show a series of pharmacological actions: n-3 PUFA ocean glyceryl ester can significantly reduce triglyceride level and vldl level in the blood plasma, regulating blood fat in human body; Can reduce systolic pressure, reduce the initiation potential of cardiovascular disorder; Improve function of vascular endothelium, strengthen the expansion of blood vessel endothelium dependency, increase blood flow volume; Anti-inflammatory, anti-platelet aggregation effect; Brain tonic and intelligence development etc.
American-European and Japan and other countries is reported more to the research of n-3 PUFA ocean glyceryl ester, and the research of China still is in the starting stage, and the research report is less, and the ocean glyceryl ester of high-content n-3PUFA yet there are no product and comes out.China mainly is selective hydrolysis or the transesterify of adopting lipase to the research of preparation n-3PUFA ocean glyceryl ester, and the research that utilizes lipase-catalyzed synthetic method to prepare n-3PUFA ocean glyceryl ester also is in blank.
Summary of the invention
The purpose of this invention is to provide the method that a kind of enzyme process prepares n-3PUFA ocean glyceryl ester, refined fish oil is prepared n-3PUFA enriched material, lipase-catalyzed n-3PUFA and glycerine building-up reactions, extracting and separating n-3PUFA ocean glyceryl ester through saponification, acidifying, urea adduct method, n-3PUFA effectively is enriched in the glyceryl ester, makes to have and prevent and functional products such as treatment cardiovascular disorder, brain tonic and intelligence development.
Purpose of the present invention can realize by following technological measure:
1, the preparation of n-3PUFA enriched material
Refined fish oil utilizes the sodium hydroxide ethanolic soln to carry out saponification and handles, and utilizes sulfuric acid acidation then, prepares the enriched material that contains 50%～80%n-3PUFA with urea adduct method again.
2, lipase-catalyzed n-3PUFA and glycerine building-up reactions
Normal hexane and glycerine ratio 4～1/1 (v/w), n-3 PUFA and glycerine ratio 10%～25% (w/w), the water of 0.3%～0.8% (w/w), lipase Novozym435 is 4%～12% (w/w) of n-3 PUFA, 30～50 ℃ are reacted with 150rpm concussion under nitrogen protection, add 0.5～1g molecular sieve behind the 1h; Reaction 12-24h gets reaction product.
3, the ocean glyceryl ester of extracting and separating n-3PUFA
Reaction product is filtered through the anhydrous sodium sulphate bed, removes lipase and molecular sieve; With in the standard caustic soda solution and free fatty acids; With n-hexane extraction n-3PUFA ocean glyceryl ester; Remove solvent with the Rotary Evaporators decompression, obtain n-3PUFA ocean glyceryl ester.
The present invention has the following advantages:
1, raw material n-3PUFA of the present invention is from natural fish oil, and is safe and effective, adopts the inflated with nitrogen protection in the production process and do not add synthetized oxidation preventive agent, effectively prevented the oxidation of n-3PUFA;
2, the technology of the present invention craft science is reasonable, utilizes biological enzyme to synthesize, and the gamma value height of reaction has improved utilization ratio of raw materials, and reaction process is easy to control;
3, main component has monoglyceride, triglyceride and triglyceride level in the n-3PUFA ocean glyceryl ester of the present invention's preparation; The triglyceride compound is based on the 1-DHA-3-DHA-triglyceride; Triglyceride compound is based on 1-DHA-2-DHA-3-DHA-triglyceride level and 1-EPA-2-DHA-3-DHA-triglyceride level;
4, the physical and chemical index of the n-3 PUFA ocean glyceryl ester of the present invention's preparation has reached the standard of food oils, and the total content of DHA and EPA can reach 50% ~ 80%; Can be developed into to have and prevent and functional products such as treatment cardiovascular disorder, brain tonic and intelligence development, have vast market prospect.
Embodiment
The present invention is described further in conjunction with the implementing process example, but these examples are not done any qualification to the present invention.
Example 1:
In reaction vessel, add normal hexane 7mL; glycerine 5g; n-3 PUFA enriched material 1g is (from tuna fish oil; DHA and EPA content are respectively 72% and 17%), the water of 0.6% (w/w), 40mg lipase Novozym435; at the nitrogen protection lower seal; in 40 ℃ water bath with thermostatic control shaking table, carry out esterification, after question response carries out 1h, add the 1g molecular sieve and remove the moisture that dereaction generates with 150 times/min.After question response finishes; lipase-catalyzed synthetic reaction mixture is filtered by the anhydrous sodium sulphate bed; remove enzyme molecule and molecular sieve; filtrate is blush with 0.025mol/L sodium hydroxide solution titration (phenolphthalein is made indicator) to solution, and reaction solution is transferred in the separating funnel, adds the 25mL normal hexane; mix; discard lower aqueous solution, collect upper strata normal hexane layer (containing acylglycerol), use anhydrous sodium sulfate dehydration again.Under 45 ℃ of conditions, remove normal hexane then and promptly get n-3PUFA ocean glyceryl ester with Rotary Evaporators.Detect through silica gel column chromatography, diglyceride content is 56% in the glyceryl ester of n-3PUFA ocean; Triglyceride level 31% and monoglyceride 13%; Through gas chromatographic analysis, DHA content is 70% in the glyceryl ester of n-3PUFA ocean.EPA content is 15%.
Example 2:
In reaction vessel, add normal hexane 5mL; glycerine 3g; n-3 PUFA enriched material 0.5g is (from stripped tuna fish oil; DHA and EPA content are respectively 68% and 15%), the water of 0.5% (w/w), 20mg lipase Novozym435; at the nitrogen protection lower seal; in 40 ℃ water bath with thermostatic control shaking table, carry out esterification, after question response carries out 1h, add the 1g molecular sieve and remove the moisture that dereaction generates with 150 times/min.After question response finishes; lipase-catalyzed synthetic reaction mixture is filtered by the anhydrous sodium sulphate bed; remove enzyme molecule and molecular sieve; filtrate is blush with 0.025mol/L sodium hydroxide solution titration (phenolphthalein is made indicator) to solution, and reaction solution is transferred in the separating funnel, adds the 25mL normal hexane; mix; discard lower aqueous solution, collect upper strata normal hexane layer (containing acylglycerol), use anhydrous sodium sulfate dehydration again.Under 45 ℃ of conditions, remove normal hexane then and promptly get n-3PUFA ocean glyceryl ester with Rotary Evaporators.Detect through silica gel column chromatography, diglyceride content is 53% in the glyceryl ester of n-3PUFA ocean; Triglyceride level 35% and monoglyceride 12%; Through gas chromatographic analysis, DHA content is 65% in the glyceryl ester of n-3PUFA ocean.EPA content is 17%.
Example 3:
In reaction vessel, add normal hexane 10mL; glycerine 7g; n-3 PUFA enriched material 1g is (from snake grey mullet oil; DHA and EPA content are respectively 48% and 20%), the water of 0.8% (w/w), 80mg lipase Novozym435; at the nitrogen protection lower seal; in 40 ℃ water bath with thermostatic control shaking table, carry out esterification, after question response carries out 1h, add the 1g molecular sieve and remove the moisture that dereaction generates with 150 times/min.After question response finishes; lipase-catalyzed synthetic reaction mixture is filtered by the anhydrous sodium sulphate bed; remove enzyme molecule and molecular sieve; filtrate is blush with 0.025mol/L sodium hydroxide solution titration (phenolphthalein is made indicator) to solution, and reaction solution is transferred in the separating funnel, adds the 25mL normal hexane; mix; discard lower aqueous solution, collect upper strata normal hexane layer (containing acylglycerol), use anhydrous sodium sulfate dehydration again.Under 45 ℃ of conditions, remove normal hexane then and promptly get n-3PUFA ocean glyceryl ester with Rotary Evaporators.Detect through silica gel column chromatography, diglyceride content is 49% in the glyceryl ester of n-3PUFA ocean; Triglyceride level 32% and monoglyceride 19%; Through gas chromatographic analysis, DHA content is 46% in the glyceryl ester of n-3PUFA ocean.EPA content is 18%.
Claims (4)
1. plant the method that enzyme process prepares n-3PUFA ocean glyceryl ester, it is characterized in that comprising following processing step:
(1) preparation of n-3PUFA enriched material
Refined fish oil utilizes the sodium hydroxide ethanolic soln to carry out saponification and handles, and utilizes sulfuric acid acidation then, prepares 50%～80%n-3PUFA enriched material with urea adduct method again;
(2) lipase-catalyzed n-3PUFA and glycerine building-up reactions
Normal hexane and glycerine ratio 4～1/1v/w, n-3 PUFA and glycerine ratio 10%～25%w/w, the water of 0.3%～0.8% w/w, lipase Novozym435 is 4%～12%w/w of n-3 PUFA, 30～50 ℃ are reacted with 150rpm concussion under nitrogen protection, add 0.5～1g molecular sieve behind the 1h; Reaction 12-24h gets reaction product;
(3) the ocean glyceryl ester of extracting and separating n-3PUFA
Reaction product is filtered through the anhydrous sodium sulphate bed, removes lipase and molecular sieve; With in the standard caustic soda solution and free fatty acids; With n-hexane extraction n-3PUFA ocean glyceryl ester; Remove solvent with the Rotary Evaporators decompression, obtain n-3PUFA ocean glyceryl ester.
2. the method for preparing n-3PUFA ocean glyceryl ester according to the described a kind of enzyme process of claim 1, it is characterized in that in reaction vessel, adding normal hexane 7mL, glycerine 5g, tuna fish oil n-3 PUFA enriched material 1g, wherein DHA and EPA content are respectively 72% and 17%, the water of 0.6%w/w, 40mg lipase Novozym435, at the nitrogen protection lower seal, in 40 ℃ water bath with thermostatic control shaking table, carry out esterification with 150 times/min, after question response carries out 1h, add the 1g molecular sieve and remove the moisture that dereaction generates; Question response filters lipase-catalyzed synthetic reaction mixture after finishing by the anhydrous sodium sulphate bed, remove enzyme molecule and molecular sieve, filtrate is used the titration of 0.025mol/L sodium hydroxide solution, phenolphthalein is made indicator, is blush to solution, and reaction solution is transferred in the separating funnel, add the 25mL normal hexane, mix, discard lower aqueous solution, collect upper strata normal hexane layer, contain acylglycerol, use anhydrous sodium sulfate dehydration again; Under 45 ℃ of conditions, remove normal hexane then and promptly get n-3PUFA ocean glyceryl ester with Rotary Evaporators; Detect through silica gel column chromatography, diglyceride content is 56% in the glyceryl ester of n-3PUFA ocean; Triglyceride level 31% and monoglyceride 13%; Through gas chromatographic analysis, DHA content is 70% in the glyceryl ester of n-3PUFA ocean; EPA content is 15%.
3. the method for preparing n-3PUFA ocean glyceryl ester according to the described a kind of enzyme process of claim 1, it is characterized in that in reaction vessel, adding normal hexane 5mL, glycerine 3g, stripped tuna fish oil n-3 PUFA enriched material 0.5g, wherein DHA and EPA content are respectively 68% and 15%, the water of 0.5%w/w, 20mg lipase Novozym435, at the nitrogen protection lower seal, in 40 ℃ water bath with thermostatic control shaking table, carry out esterification with 150 times/min, after question response carries out 1h, add the 1g molecular sieve and remove the moisture that dereaction generates; Question response filters lipase-catalyzed synthetic reaction mixture after finishing by the anhydrous sodium sulphate bed, remove enzyme molecule and molecular sieve, filtrate is with the titration of 0.025mol/L sodium hydroxide solution, and phenolphthalein is made indicator, is blush to solution, reaction solution is transferred in the separating funnel, add the 25mL normal hexane, mix, discard lower aqueous solution, collect upper strata normal hexane layer, contain acylglycerol,, use anhydrous sodium sulfate dehydration again; Under 45 ℃ of conditions, remove normal hexane then and promptly get n-3PUFA ocean glyceryl ester with Rotary Evaporators; Detect through silica gel column chromatography, diglyceride content is 53% in the glyceryl ester of n-3PUFA ocean; Triglyceride level 35% and monoglyceride 12%; Through gas chromatographic analysis, DHA content is 65% in the glyceryl ester of n-3PUFA ocean; EPA content is 17%.
4. the method for preparing n-3PUFA ocean glyceryl ester according to the described a kind of enzyme process of claim 1, it is characterized in that in reaction vessel, adding normal hexane 10mL, glycerine 7g, snake grey mullet n-3 PUFA enriched material 1g, wherein DHA and EPA content are respectively 48% and 20%,, the water of 0.8%w/w, 80mg lipase Novozym435, at the nitrogen protection lower seal, in 40 ℃ water bath with thermostatic control shaking table, carry out esterification, after question response carries out 1h, add the 1g molecular sieve and remove the moisture that dereaction generates with 150 times/min; Question response filters lipase-catalyzed synthetic reaction mixture after finishing by the anhydrous sodium sulphate bed, remove enzyme molecule and molecular sieve, filtrate is used the titration of 0.025mol/L sodium hydroxide solution, phenolphthalein is made indicator, is blush to solution, and reaction solution is transferred in the separating funnel, add the 25mL normal hexane, mix, discard lower aqueous solution, collect upper strata normal hexane layer, contain acylglycerol, use anhydrous sodium sulfate dehydration again; Under 45 ℃ of conditions, remove normal hexane then and promptly get n-3PUFA ocean glyceryl ester with Rotary Evaporators; Detect through silica gel column chromatography, diglyceride content is 49% in the glyceryl ester of n-3PUFA ocean; Triglyceride level 32% and monoglyceride 19%; Through gas chromatographic analysis, DHA content is 46% in the glyceryl ester of n-3PUFA ocean; EPA content is 18%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100308629A CN101161819A (en) | 2007-10-12 | 2007-10-12 | Method for preparing n-3PUFA ocean glycerin ester by enzymatical process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100308629A CN101161819A (en) | 2007-10-12 | 2007-10-12 | Method for preparing n-3PUFA ocean glycerin ester by enzymatical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101161819A true CN101161819A (en) | 2008-04-16 |
Family
ID=39296804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007100308629A Pending CN101161819A (en) | 2007-10-12 | 2007-10-12 | Method for preparing n-3PUFA ocean glycerin ester by enzymatical process |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101161819A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101736044A (en) * | 2008-11-18 | 2010-06-16 | 浙江海洋学院 | Method for continuous enzymatic synthesis of n-3PUFA glyceride |
| CN102028711A (en) * | 2010-12-27 | 2011-04-27 | 河北康睿达脂质有限公司 | Enzymatically synthesized triglyceride type fish oil soft capsules and preparation method thereof |
| CN101348807B (en) * | 2008-08-26 | 2011-07-27 | 江南大学 | Method for enrichment of n-3 polyunsaturated fatty acid glyceride from fish oil |
| CN104651422A (en) * | 2013-11-20 | 2015-05-27 | 深圳市中科海世御生物科技有限公司 | Method of extracting DHA and EPA in type of triglyceride from deep-sea fish |
| CN106755149A (en) * | 2016-11-29 | 2017-05-31 | 大连工业大学 | A kind of method that utilization lipase prepares hydroxytyrosol DHA ester |
| US10030212B2 (en) | 2014-10-13 | 2018-07-24 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Method for preparing glyceride type polyunsaturated fatty acids |
| CN111172208A (en) * | 2020-03-11 | 2020-05-19 | 陕西科技大学 | Method for preparing 2-monoglyceride type n-3PUFA by enzyme method |
-
2007
- 2007-10-12 CN CNA2007100308629A patent/CN101161819A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101348807B (en) * | 2008-08-26 | 2011-07-27 | 江南大学 | Method for enrichment of n-3 polyunsaturated fatty acid glyceride from fish oil |
| CN101736044A (en) * | 2008-11-18 | 2010-06-16 | 浙江海洋学院 | Method for continuous enzymatic synthesis of n-3PUFA glyceride |
| CN101736044B (en) * | 2008-11-18 | 2013-10-23 | 浙江海洋学院 | Method for continuous enzymatic synthesis of n-3PUFA glyceride |
| CN102028711A (en) * | 2010-12-27 | 2011-04-27 | 河北康睿达脂质有限公司 | Enzymatically synthesized triglyceride type fish oil soft capsules and preparation method thereof |
| CN104651422A (en) * | 2013-11-20 | 2015-05-27 | 深圳市中科海世御生物科技有限公司 | Method of extracting DHA and EPA in type of triglyceride from deep-sea fish |
| CN104651422B (en) * | 2013-11-20 | 2018-02-27 | 深圳市海优康生物科技有限公司 | A kind of method that triglyceride type DHA and EPA are extracted from deep-sea fish |
| US10030212B2 (en) | 2014-10-13 | 2018-07-24 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Method for preparing glyceride type polyunsaturated fatty acids |
| CN106755149A (en) * | 2016-11-29 | 2017-05-31 | 大连工业大学 | A kind of method that utilization lipase prepares hydroxytyrosol DHA ester |
| CN111172208A (en) * | 2020-03-11 | 2020-05-19 | 陕西科技大学 | Method for preparing 2-monoglyceride type n-3PUFA by enzyme method |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101348807B (en) | Method for enrichment of n-3 polyunsaturated fatty acid glyceride from fish oil | |
| CN101161819A (en) | Method for preparing n-3PUFA ocean glycerin ester by enzymatical process | |
| CN104651422B (en) | A kind of method that triglyceride type DHA and EPA are extracted from deep-sea fish | |
| CN101845362B (en) | Method for gathering oleic acid from tea-seed oil | |
| CN104186705B (en) | Method based on enzymatic acidolysis palmitic acid three Lipase absobed structured lipid | |
| CN111088296B (en) | Method for enriching n-3 polyunsaturated fatty acid glyceride in grease | |
| MY145667A (en) | Process for producing fatty acid alkyl esters and glycerin | |
| CN102224854A (en) | Method for producing flaxseed oil under nitrogen protection | |
| CN101607977A (en) | Extract the method and the technology of purifying natural plant sterol in the oil deodorization distillate residual oil | |
| CN107216252A (en) | A kind of preparation method of high content Omega-3 fatty-acid ethyl esters | |
| CN102994580B (en) | Preparation method of high-purity triglyceride type PUFA (Polyunsaturated Fatty Acid) | |
| CN102320953B (en) | Method for preparing natural alpha-linolenic acid from crude oil of idesia polycarpa var.vestita diels | |
| CN102277237B (en) | Preparation method of high-purity glyceride type fish oil | |
| CN104846023A (en) | Method for preparing concentrated fish oil fatty acid glyceride | |
| CN101774997A (en) | Method for completely and continuously extracting natural vitamin E and phytosterol | |
| CN102603845A (en) | Method for synthesizing and separating phytosterol saturated fatty acid esters and phytosterol unsaturated fatty acid esters | |
| CN107823137A (en) | A kind of preparation method of injection refined fish oil | |
| CN104151282A (en) | Method for preparing natural vitamin E and phytosterol with resin absorption method | |
| CN105062694B (en) | A kind of method that C18 series fatty acids and C20~C22 series fatty acids finely detach | |
| CN101381398A (en) | Supercritical extraction method of soybean phytosterol material by CO2 | |
| CN110004188A (en) | A method of preparing PUFAs glyceride from the crude oil that microbial fermentation obtains | |
| CN108531538A (en) | A kind of method that enzyme process prepares phytosterin ester | |
| CN100510041C (en) | Preparation process of high content conjugated unsaturated trienic acid granada seed oil | |
| CN115010572A (en) | Method for extracting squalene and vitamin E | |
| CN106748780B (en) | A kind of removal methods of injection Synthetic Oil metal residual |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20080416 |