CN103113446A - Method for separating and extracting sterol from wool fat - Google Patents
Method for separating and extracting sterol from wool fat Download PDFInfo
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- CN103113446A CN103113446A CN2013100825211A CN201310082521A CN103113446A CN 103113446 A CN103113446 A CN 103113446A CN 2013100825211 A CN2013100825211 A CN 2013100825211A CN 201310082521 A CN201310082521 A CN 201310082521A CN 103113446 A CN103113446 A CN 103113446A
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Abstract
The invention discloses a method for separating and extracting sterol from wool fat. The method comprises the following step of: (1), carrying out saponification reaction on the wool fat in an alkali-alcohol solution; (2), carrying out saponification double decomposition on calcium chloride and the product obtained in the last step to obtain a calcium soap and wool alcohol; (3), filtering the obtained filtrate in vacuum, extracting under refluxing filter residue by utilizing low-level fatty alcohol, collecting filtrate and adding fatty acid to the filtrate to remove the residual calcium ion; (4), acidifying and bleaching filter cake to obtain the wool acid; and (5), carrying out recrystallization to obtain a refined product. The steps are carried out, so that the purity of obtained cholesterol is higher than 93% and the yield is more than 78%. The method disclosed by the invention has the advantages that the obtained product is high in purity and yield, excellent in color and crystal form and free of peculiar smell, the process flow is simple and easy to operate, and the solvent and the chromatography media in the process flow can be recycled without generating wastes, so that the process cost is low and the industrial production can be realized.
Description
Technical field
The invention belongs to biochemical detaching direction, be used for from lanolin separation and Extraction sterol, specifically refer to obtain the method for the sterols such as high quality cholesterol, lanosterol through saponification → metathesis → solvent slective extraction → column chromatography → techniques such as recrystallization.
Background technology
The natural materials that cholesterol is known as a kind of people owing to having multifrequency nature, makes it be widely used at makeup, material, biomedicine field.1. from biological factor aspect analysis, the cholesterol cell membrane has affinity interaction, and can change the character of cytolemma, and this is significant in the application aspect Thermosensitive Material Used for Controlled Releasing of Medicine and organizational project for polymkeric substance.2. important pharmaceutical intermediate, be mainly used in synthesis of vitamin d
3, steroid drugs and dependency hormone etc.3. cholesterol has mulitiple chiral centers, and its derivative (ethers, ester class, halogenide, carbonic ether etc.) can form the aggregate of various uniquenesses, comprises liquid crystal, organogel and unimolecular layer, special cholest-class liquid crystal molecule.4. cholesterol has oilness to skin, and its unique structure can absorb free radical, so cholesterol can be used as the additive of makeup and sunscreen.
1. the production technique of present cholesterol has extracts from animal brain and myeloid tissue.Because the leaching process cost is high, not environmental protection, and the product that obtains is limited, limits it and further develop; 2. extract from wool washing waste water, its complex process, benefit are low; 3. extract from lanolin, its raw material sources are extensive, and are with low cost, are easy to produce.
Lanolin is the smegma thing of sheep, is deposited on wool fiber.Degras is a kind of brown, dope frowzy, is that yellow is translucent, the thickness body of paste of oiliness after making with extra care.Fusing point is 39 ~ 42 ℃; Water-soluble hardly, but can absorb the moisture that is equivalent to 2 times of own wts; Lanolin is soluble in ether, benzene, chloroform, acetone, sherwood oil, and is hard to tolerate in cold alcohol, dissolves in heat alcohol, can be used as cosmetic emollients, permeate agent, emulsifying agent etc.; Can obtain the higher fatty acid for the automobile chassis coating after refining; Also can be used as gas-chromatography low-pole stationary liquid, be used for the analysis of non-polar compound.
Lanolin is known as again " soft gold ", and its each composition all has widely to be used.The lanolin composition can be divided into lanolin fatty acid and the large class of lanosterol two.In lanosterol, except cholesterol and Fatty Alcohol(C12-C14 and C12-C18), lanosterol has good perviousness, water-absorbent and lubricity etc., and mainly as the additive of the cosmetics of super quality, lipstick, fragrant body cream, lipstick etc., and its price is considerable, is the product of high value.
In last century, after lanolin mainly passes through and makes with extra care at home, as lubricant or rudimentary cosmetics additive, value added is very low.As mentioned above, the materials such as the cholesterol that lanolin obtains after separation and purification, lipid acid, lanosterol are all the products with high additive value, more are conducive to the future development of this industrial chain.With regard to present progress of research, in lanolin, the general step of cholesterol separation and purification is: saponification/transesterification → pure soap separates → separates cholesterol → recrystallizing and refining.
According to present domestic and international progress, in lanolin, the separating and extracting method of cholesterol is a feast for the eyes, seeing report just has 8 kinds of left and right, is respectively molecular distillation, supercritical fluid extraction, bromination method, solvent selective freezing, adsorpting column chromatography, partition column chromatography, complex compound method cyclodextrin method etc.
Separate at lanosterol and lanolin fatty acid, the product Extraction parts: the Xiamen CN 101085716A of Jin Dawei house journal has described a kind of method that lanosterol and lanolin fatty acid separate of completing, the contriver utilizes the liquid-liquid extraction tower, lanolin saponification product is carried out continuous extraction, reaching both separates, experimental procedure is simple, but Solvent quantity is large, and recovery utilization rate is low, and the not further further separation of research crude product.Utilize the solvent slective extraction to complete separating of lanosterol and lanolin fatty acid in the patent CN 1594350A of Zhejiang University, then utilize the method separation of solvent selective freezing to obtain thick cholesterol, the major defect of the method is that will to control parameter in experimentation more, and the more difficult control of major part is as the screening of experiment service temperature, solvent for use, solvent load, and crystallization operation parameter etc.Patent CN 1884460A is the problem of avoiding using in experimentation acid base catalysator, utilizes in critical aqueous medium, and hydrolysis preparation lanosterol and lanolin fatty acid, process is simple, but service temperature is too high.The patent CN 101817859A of University Of Tianjin is that directly to adopt Wool wax alcohol be starting raw material, utilizes molecular distillation to obtain refining lanosterol, and then take methyl alcohol and acetone as solvent, the adjusting ratio obtains cholesterol after the multistep selective freezing.The consumption of the method chemical adjuvant is few, but the molecule rectifying device is expensive, and the difficult control of solvent slective extraction conditional parameter.The patent CN 1958596A of Zhejiang University has described column chromatography method and has reached product separation, first lanolin is carried out transesterification, then carry out short-path distillation, obtain the cholesterol crude product, wet method loading then is take 90 ~ 120 order silica gel as chromatography media, (ratio is 70:30 ~ 95:5) carry out wash-out for moving phase for toluene and sherwood oil, obtain purity and be 88% ~ 90% cholesterol, experimentation transfer esterification section obtains the easy emulsification of soda soap, makes soap and pure separation difficulty; Short-path distillation relates to gradient increased temperature, and outlet temperature is at 200 ℃, operational hazards in industrialization; The column chromatography step adopts operate continuously, isocratic elution, can complete the separation of sterols, but purity is not high, and manipulation require carries out under 30 ℃ of constant temperature again, design to chromatography column has just proposed further requirement, and the design of pillar in industrialization has been proposed larger challenge.
Be emulsification, column chromatography sample thickness, column chromatography constant temperature method, the product separation purity not high in esse problem of solution soda soap to reaction solution, so this patent relates to the method that overcomes the above problems and obtain the high purity sterol.
Summary of the invention
Content of the present invention relates to the product separation purifying techniques such as " lanolin saponification → metathesis → pure soap separation → calcium soap acidifying/solvent slective extraction → column chromatography for separation sterol → product recrystallization " this cholesterol, lanosterol.
Cholesterol separation purifying technique in the present invention comprises the following steps:
1) lanolin saponification: (lanolin and alkali mol ratio are 1:1.3 ~ 1:2) be added in reaction vessel to take the alkali of respective amount, and add appropriate amount Fatty Alcohol(C12-C14 and C12-C18) (6 ~ 10mL/g lanolin) and water (0 ~ 4 mL/g lanolin) as solvent, the lanolin that adds while stirring brown molten state, stirring reaction is 3 ~ 8 hours under 78 ~ 85 ℃ of conditions, the reaction solution color is deepened gradually, obtains the brownish black mixing solutions after end.
2) calcium soap transforms: between cooling above-mentioned reaction solution to 40 ~ 55 ℃, and after utilizing inorganic acid for adjusting pH value to be 8.5 left and right, take the calcium salt of 0.5 times (with respect to sodium hydroxide concentration), stirring reaction 1 ~ 2 hour obtains dark brown mixture.
3) pure soap separates: after the mixture suction filtration, utilize dehydrated alcohol to carry out twice extraction residue, merge the dark brown filtrate and the khaki color filter residue that obtain.
4) calcium soap acidifying: after the lanolin fatty acid soap that obtains is dissolved, and be heated to 50 ~ 60 ℃ in lower paraffin hydrocarbons, add the mineral acid of specified quantitative, stirring reaction 15 ~ 30min carries out suction filtration while hot, obtains white or faint yellow solid and dark-brown liquid.
5) lanolin fatty acid is refining: be divided into three layers after dark-brown liquid washes with water, upper strata (dark-brown) and middle level (light yellow) obtains light yellow solid after concentrating, and is accredited as lanolin fatty acid; Lower floor is water.
6) solvent slective extraction: lanosterol is dissolved in lower paraffin hydrocarbons, be heated to reflux, (acetic acid and lower paraffin hydrocarbons ratio are 1:4 ~ 1:8), obtain light brown liquid and part white solid after stirring to add acetic acid, after suction filtration, filtrate is concentrated, obtain yellow solid (lanosterol).
7) column chromatography: add a small amount of silica-gel powder after the lanosterol that obtains is dissolved with moving phase, revolve and steam to dry.Dry method loading, or directly with the paste substance loading, take lower paraffin hydrocarbons and ethyl acetate as moving phase, adjust its ratio from 100%, 30:1,20:1,10:1 carry out gradient elution, carries out simultaneously thin-layer chromatography and identify, collect same composition and also concentrate.Can obtain successively not saponification lanolin, Fatty Alcohol(C12-C14 and C12-C18), lanosterol, cholesterol, unknown sterol etc.
8) product purification: with components such as cholesterol, lanosterol, utilize lower alcohol or complex solvent to carry out recrystallization with the ratio of 1:5 ~ 1:10, obtain white needle-like crystals after drying, carry out corresponding construction and identify.
Lower aliphatic hydrocarbon described in the present invention is sherwood oil, normal hexane, Skellysolve A etc.; The lower fatty acid extraction agent is acetic acid; Mineral acid refers to 30% ~ 38% hydrochloric acid, the vitriol oil, phosphoric acid etc.; Step 8) in, lower alcohol used refers to 90 ~ 98% ethanol, dehydrated alcohol, methyl alcohol etc., and complex solvent refers to the composite use of the lower paraffin hydrocarbonss such as sherwood oil, normal hexane, Skellysolve A and ethyl acetate, methyl alcohol etc.
Compare with other method that prior art is known, this programme has in following advantage one or all at least:
1) operational path is simple and easy to operate.Present method co-exists in three large operating units: saponification unit, separating unit, refined unit, and whole operation is completed only needs about 18 ~ 24 hours, and in general, route is simple and there is no a complicated operation.
2) solved the emulsification of soda soap to reaction system in the saponification reaction, made the later separation hard problem.
3) recrystallization makes that product yield is high, crystal formation is good, color and luster is good, satisfies medical production requirement.The present lab scale craft of present method, the cholesterol purity that obtains satisfies the drug manufacture requirement higher than 93%.
4) productive rate is high, and production cost is low, is convenient to suitability for industrialized production.The productive rate of the cholesterol that present method obtains at present is more than 80%, and the larger room for promotion of existence; And the solvent that uses in technique, chromatography media are all recyclable, and running cost is reduced greatly, thereby guarantee that it is convenient to scale-up and suitability for industrialized production in the future.
Description of drawings
Fig. 1: lanolin process for separating and purifying schema.
Embodiment
The following examples can make the professional and technical personnel more understand the present invention.
Embodiment 1
1. take 25.000 g lanolin (contain cholesterol approximately 11%), put into 250 mL there-necked flasks, add 150 mL ethanol and 2.679 g sodium hydroxide and 10 mL deionized waters, be heated to reflux temperature (80 ℃), mechanical stirring reaction 3-8 hour, reaction finishes to obtain the brownish black mixing solutions.
2. reducing reacting liquid temperature is 40 ~ 55 ℃, and conditioned reaction liquid pH value is about 8.5 ~ 9, take the calcium chloride of 0.5 times of molar weight (with respect to sodium hydroxide concentration), stirring reaction 1 ~ 2 hour, the reaction solution color shoals gradually, obtain deep yellow mixture (can obtain black residue more than 70 ℃, be unfavorable for reacting and carry out).
3. after the mixture suction filtration, residue is recycled dehydrated alcohol (200 mL * 3) extract, obtain khaki color calcium soap powder, merge all deep yellow filtrates and concentrate and obtain the deep yellow thick liquid.
4. the khaki color calcium soap powder lanolin fatty acid soap that obtains is dissolved in sherwood oil, and be heated to 40 ~ 50 ℃, add 8 ~ 10mL, 36% hydrochloric acid under continuing to stir, after stirring reaction 15 ~ 20min, carry out while hot suction filtration, obtain white solid (carry out infrared identification after solid drying, be fatty acid calcium) and dark-brown liquid.
5. be divided into three layers after dark-brown liquid washes with water, upper strata (dark-brown) and middle level (yellow) forms colloidal solid at low temperatures, is accredited as lanolin fatty acid, and molten state is brownish black; Lower floor is water.
6. lanosterol (the deep yellow thick liquid that the 3rd step obtained) is dissolved in sherwood oil, be heated to reflux, add 50 mL acetic acid, obtain light brown liquid and a small amount of white solid (after dry, infrared identification is calcium acetate) after stirring, after suction filtration, filtrate is concentrated, obtain refining lanosterol.
7. will make with extra care lanosterol and add a small amount of silica-gel powder after with petroleum ether dissolution, and revolve and steam to dry.The dry method loading take sherwood oil and ethyl acetate as moving phase, is adjusted sherwood oil and is carried out gradient elution with the ethyl acetate ratio, during first with 100% sherwood oil wash-out, can obtain not saponification lanolin after consuming 500ml; After identifying with thin-layer chromatography, use the 30:1(all proportions instead and all refer to sherwood oil: ethyl acetate) carry out wash-out, approximately consume popular phase 3L, can obtain the Fatty Alcohol(C12-C14 and C12-C18) component; Next is used 20:1 moving phase instead and carries out wash-out, carries out simultaneously thin-layer chromatography and detects, and guarantees that cholesterol components does not flow out, and approximately consumes 1.5L moving phase, can obtain the lanosterol component; Then use 10:1 moving phase instead and carry out wash-out, approximately consume 2.0L moving phase, can obtain cholesterol components; Carry out wash-out with 100% ethyl acetate of about 1L at last, carry out at any time thin-layer chromatography and identify, see whether also have product to be washed out (the thin-layer chromatography demonstration washes out without product).
8. the lanosterol component and the cholesterol components that previous step (the 7th step) are obtained, utilize dehydrated alcohol (5mL/g) to carry out recrystallization, cholesterol/crude lanosterol product is put into round-bottomed flask, first add a small amount of ethanol, then be heated to reflux, after dropping ethanol to all powder dissolves fully, then add the total amount into 10 ~ 20%(), naturally cooling or subcooling in refrigerator.Finally obtain the 2.15g cholesterol, purity 92.6%(productive rate＞78%), and the 0.801g lanosterol.
Embodiment 2
Recrystallization operated the step 1-7 with example 1 before the step.With the cholesterol crude product that obtains, being heated to reflux is dissolved in (8mL/g) in ethyl acetate, after the solution clarification, dropwise add again sherwood oil, when adding sherwood oil just to make solution muddy, be heated to clarification, be cooled to crystal and separate out, finally obtain the 2.07g cholesterol, purity 92.2%.
Embodiment 3
Recrystallization operated the step 1-7 with example 1 before the step.With the cholesterol crude product that obtains, being heated to reflux is dissolved in (5mL/g) in dehydrated alcohol, after the solution clarification, dropwise add again entry, when adding sherwood oil just to make solution muddy, be heated to clarification, be cooled to crystal and separate out, finally obtain the 2.21g cholesterol, purity 93.0%.
Embodiment 4
Recrystallization operated the step 1-7 with example 1 before the step.With the cholesterol crude product that obtains, being heated to reflux is dissolved in (10mL/g) in anhydrous methanol, after dropping methyl alcohol to all powder dissolves fully, then adds the total amount into 10%(), naturally cool to crystal and separate out, finally obtain the 1.93g cholesterol, purity 95.2%.
What need to understand is: although above-mentioned example is to the present invention's detailed description of contrasting; but these descriptions are the simple description to thinking of the present invention; rather than to the restriction of this novel thinking of sterol in column chromatography for separation lanolin; any combination that does not exceed thinking of the present invention increases or modification all falls into protection scope of the present invention.
Claims (8)
1. the method for separation and Extraction sterol from lanolin, is characterized in that comprising the steps:
1. saponification reaction: as solvent, take alkali with lower aliphatic alcohols, control temperature at 50 ~ 60 ℃, be added dropwise to the lanolin of molten state, randomly drip a small amount of water, be warming up to 78 ~ 85 ℃, under normal pressure, stirring reaction 3 ~ 8h obtains dark brown mixture;
2. saponification metathesis: 40 ~ 55 ℃ of degree of cooling above-mentioned reaction solution, regulate pH to 8-9, add calcium salt, stirring obtains calcium soap, and centrifugal or suction filtration carries out solid-liquid separation, recycles simultaneously lower aliphatic alcohols filter residue is carried out 2 ~ 3 reflux extraction, then suction filtration and collect filtrate, merge all filtrates and concentrated;
3. filter residue at 50 ~ 60 ℃, obtains the crude product lanolin fatty acid after the mineral acid acidifying, obtains refining lanolin fatty acid after common and braid wool acid is made with extra care;
4. remove residual calcium ion, reduce lanosterol viscosity: with lower paraffin hydrocarbons, ethyl acetate, methyl alcohol or ether dissolution, add lower fatty acid to stir the filtrate concentrated solution, obtain white solid, after suction filtration, oil phase is washed, be neutral to water pH, collect oil phase and concentrate;
5. the concentrated oil phase in upper step is added a small amount of silica-gel powder after with petroleum ether dissolution, revolve and steam to dry, the dry method loading is take sherwood oil and ethyl acetate as moving phase, adjust sherwood oil and carry out gradient elution with the ethyl acetate ratio, first obtain not saponification lanolin with 100% sherwood oil wash-out; With 30:1 volume ratio sherwood oil: ethyl acetate is carried out wash-out and is obtained the Fatty Alcohol(C12-C14 and C12-C18) component; Next uses 20:1 volume ratio sherwood oil instead: ethyl acetate flows and carries out mutually wash-out, obtains the lanosterol component; Then use 10:1 volume ratio sherwood oil instead: ethyl acetate flows and carries out mutually wash-out, obtains cholesterol components;
6. the lanosterol component that the upper step was obtained and cholesterol components utilize lower aliphatic alcohols to carry out recrystallizing and refining, obtain the finished product.
As claimed in claim 1 from lanolin the method for separation and Extraction sterol, it is characterized in that: step 1. 2. 6. described lower aliphatic alcoholic solvent be dehydrated alcohol, 90-98% ethanol or methyl alcohol.
As claimed in claim 1 from lanolin the method for separation and Extraction sterol, it is characterized in that: step 2. described calcium salt is Calcium Chloride Powder Anhydrous and/or hydration calcium chloride.
As claimed in claim 1 from lanolin the method for separation and Extraction sterol, it is characterized in that: step 3. described mineral acid is 30% ~ 38% hydrochloric acid, sulfuric acid or phosphoric acid etc.
As claimed in claim 1 from lanolin the method for separation and Extraction sterol, it is characterized in that: step 4. described lower fatty acid is acetic acid.
As claimed in claim 1 from lanolin the method for separation and Extraction sterol, it is characterized in that: also comprise the operation of column chromatography after 4. in step, wherein the moving phase used of column chromatography is a kind of mixture in a kind of and ethyl acetate in sherwood oil, normal hexane, normal heptane, octane, toluene, propyl acetate, butylacetate, acetone, its proportional range is volume ratio 100:1 ~ 10:1, preferably, described chromatography media is 100 ~ 200 order silica gel.
As claimed in claim 1 from lanolin the method for separation and Extraction sterol, it is characterized in that: step 6. described lower paraffin hydrocarbons is normal hexane, Skellysolve A.
As claimed in claim 1 from lanolin the method for separation and Extraction sterol, it is characterized in that step 3. described process for refining comprise the steps: common and braid wool acid water extracting and separating, wherein gluey lanolin fatty acid solid is formed in dark brown upper and yellow middle level at low temperatures; Lower floor is water, separates and removes lower floor.
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| CN103409224A (en) * | 2013-08-10 | 2013-11-27 | 新疆西部加斯特药业有限公司 | Grease rich in unsaturated fattyacid and preparation method thereof |
| CN106521529A (en) * | 2016-10-21 | 2017-03-22 | 周荣 | Preparation method for natural non-corrosive oil remover |
| CN107141331A (en) * | 2017-07-07 | 2017-09-08 | 赵厚发 | The extracting method of cholesterol in a kind of marine organisms byproduct |
| CN107325144A (en) * | 2017-06-30 | 2017-11-07 | 赵厚发 | The extracting method of cholesterol in a kind of lanolin |
| CN108485821A (en) * | 2018-05-29 | 2018-09-04 | 浙江花园生物高科股份有限公司 | The method of base catalysis synthesis and purification lanolin |
| CN108840795A (en) * | 2018-08-08 | 2018-11-20 | 江南大学 | A method of lanolin fatty acid and lanonol are prepared by lanolin |
| CN109021051A (en) * | 2017-06-12 | 2018-12-18 | 盛世泰科生物医药技术(苏州)有限公司 | Crystal form of tetracyclic triterpenoid and application thereof |
| CN109761867A (en) * | 2019-02-28 | 2019-05-17 | 四川健腾生物技术有限公司 | One kind producing vitamin D by raw material of lanolin3New industrial process |
| CN109776646A (en) * | 2019-03-04 | 2019-05-21 | 河南省科学院高新技术研究中心 | A kind of method of continuous flow upstream microchannel extraction preparation high-purity cholesterol |
| CN111686132A (en) * | 2020-06-15 | 2020-09-22 | 中山大学 | Syngnathus sterol solid dispersion and application thereof in treating cerebral apoplexy |
| CN113135972A (en) * | 2021-03-25 | 2021-07-20 | 江西天新药业股份有限公司 | Method for purifying 24-dehydrocholesterol |
| CN113201407A (en) * | 2021-05-21 | 2021-08-03 | 浙江中谱生物科技有限公司 | Method for preparing ultrapure lanolin and synchronously enriching cholesterol ester |
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| CN114426566A (en) * | 2022-01-25 | 2022-05-03 | 淮北师范大学 | Method for separating lanosterol from lanolin |
| CN114456221A (en) * | 2022-01-25 | 2022-05-10 | 淮北师范大学 | Method for separating cholesterol |
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| CN103409224A (en) * | 2013-08-10 | 2013-11-27 | 新疆西部加斯特药业有限公司 | Grease rich in unsaturated fattyacid and preparation method thereof |
| CN106521529A (en) * | 2016-10-21 | 2017-03-22 | 周荣 | Preparation method for natural non-corrosive oil remover |
| CN109021051A (en) * | 2017-06-12 | 2018-12-18 | 盛世泰科生物医药技术(苏州)有限公司 | Crystal form of tetracyclic triterpenoid and application thereof |
| CN107325144A (en) * | 2017-06-30 | 2017-11-07 | 赵厚发 | The extracting method of cholesterol in a kind of lanolin |
| CN107325144B (en) * | 2017-06-30 | 2019-11-05 | 安徽科宝生物工程有限公司 | The extracting method of cholesterol in a kind of lanolin |
| CN107141331A (en) * | 2017-07-07 | 2017-09-08 | 赵厚发 | The extracting method of cholesterol in a kind of marine organisms byproduct |
| CN108485821B (en) * | 2018-05-29 | 2021-03-26 | 浙江花园生物高科股份有限公司 | Method for synthesizing refined lanolin by base catalysis |
| CN108485821A (en) * | 2018-05-29 | 2018-09-04 | 浙江花园生物高科股份有限公司 | The method of base catalysis synthesis and purification lanolin |
| CN108840795A (en) * | 2018-08-08 | 2018-11-20 | 江南大学 | A method of lanolin fatty acid and lanonol are prepared by lanolin |
| CN109761867A (en) * | 2019-02-28 | 2019-05-17 | 四川健腾生物技术有限公司 | One kind producing vitamin D by raw material of lanolin3New industrial process |
| CN109776646A (en) * | 2019-03-04 | 2019-05-21 | 河南省科学院高新技术研究中心 | A kind of method of continuous flow upstream microchannel extraction preparation high-purity cholesterol |
| CN111686132A (en) * | 2020-06-15 | 2020-09-22 | 中山大学 | Syngnathus sterol solid dispersion and application thereof in treating cerebral apoplexy |
| CN111686132B (en) * | 2020-06-15 | 2022-06-24 | 中山大学 | Syngnathus sterol solid dispersion and application thereof in treating cerebral apoplexy |
| CN113135972A (en) * | 2021-03-25 | 2021-07-20 | 江西天新药业股份有限公司 | Method for purifying 24-dehydrocholesterol |
| CN113201407A (en) * | 2021-05-21 | 2021-08-03 | 浙江中谱生物科技有限公司 | Method for preparing ultrapure lanolin and synchronously enriching cholesterol ester |
| CN113735931A (en) * | 2021-08-27 | 2021-12-03 | 浙江花园营养科技有限公司 | Method for separating cholesterol and 24-dehydrocholesterol by complexing crystallization |
| CN114426566A (en) * | 2022-01-25 | 2022-05-03 | 淮北师范大学 | Method for separating lanosterol from lanolin |
| CN114456221A (en) * | 2022-01-25 | 2022-05-10 | 淮北师范大学 | Method for separating cholesterol |
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