CN101817859A - Method for separating and extracting cholesterol in lanolin alcohol - Google Patents
Method for separating and extracting cholesterol in lanolin alcohol Download PDFInfo
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- CN101817859A CN101817859A CN 201010189560 CN201010189560A CN101817859A CN 101817859 A CN101817859 A CN 101817859A CN 201010189560 CN201010189560 CN 201010189560 CN 201010189560 A CN201010189560 A CN 201010189560A CN 101817859 A CN101817859 A CN 101817859A
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Abstract
The invention relates to a method for separating and extracting cholesterol in lanolin alcohol, which comprises the following steps: carrying out molecular distillation on lanolin alcohol, collecting the light-phase fraction which is refined lanolin alcohol, heating the refined lanolin alcohol in a mixed solvent of methanol and acetone until the refined lanolin alcohol is completely dissolved, and cooling to cooling temperature, wherein the remainder of the filtrate after reduced pressure distillation is the primary concentrate of cholesterol; heating to dissolve the primary concentrate of cholesterol in acetone, cooling to precipitate, filtering, and carrying out reduced pressure distillation on the filtrate to recover the solvent, wherein the balance is the secondary concentrate of cholesterol; heating to dissolve the secondary concentrate of cholesterol in an alcohol solvent, cooling to cooling temperature, keeping the temperature for 6-12 hours, and vacuum-filtering to obtain the white acerose cholesterol crude product; and recrystallizing the cholesterol crude product through a methanol-acetone mixed solvent to obtain the refined cholesterol product. The refined cholesterol product selectively recrystallizes through the solvent to obtain the byproduct lanosterol accounting for 63-70% and the cholesterol product of which the purity is more than 90%.
Description
Technical field
The present invention relates to the cholesteric technical field of separation and Extraction, cholesteric separating and extracting method in particularly a kind of Wool wax alcohol.
Background technology
Cholesterol another name cholesterol, its oxidation products 7-dehydrocholesterol synthesizes vitamins D subcutaneous being subjected to after the irradiation of daylight middle-ultraviolet lamp
3, be body vitamin D therefore
3Important source; Its unique biological performance and chirality feature are one of them integral parts by its cholesteric liquid crystal as the skeleton preparation, and it has special optical characteristics makes it be with a wide range of applications in many fields such as display device and various optical elements; Natural biological activity makes cholesterol be used for makeup and can play skin moisten, sun-proof, pore refining, alleviate wrinkle and make skin recover elastic effect.
Wool wax alcohol is the product after the lanolin saponification, contains 20～30% cholesterol, and 25～30% triterpene alcohol is the important source of natural steroid.
From Wool wax alcohol, separate cholesteric method at present and mainly contain companion method, chromatography, supercutical fluid method, solvent extration and solvent selectivity crystallization process.
Patent documentation CZ 237195 (1983) and PL 164762 (1992) have reported that applied metal muriate (calcium chloride, magnesium chloride and zinc chloride) and phytosterin compound form title complex, title complex just can obtain cholesteric technology through hydrolysis after precipitating and separating out in solvent.Though this method has suitability for industrialized production and is worth, the alcohol compound that other in the Wool wax alcohol contain β-OH can form title complex, and the cholesterol purity that obtains of hydrolysis is not high thus, and process is loaded down with trivial details to cause cholesteric yield not high.And the application of metal chloride is bigger, and production process can produce the waste water of reluctant metal ion, contaminate environment.
Among the Chinese patent ZL 200410025654.6 with the hydrocarbon of Wool wax alcohol or halohydrocarbon solution after the alcoholic solution washing, direct crystallization is separated out cholesterol under the prerequisite that the quality of Wool wax alcohol is greatly improved.This method needs extraction repeatedly, and solvent load is very big, and yield is lower, and the industry's enlarging production of extraction process needs the post-installation review of long period.
European patent EP 53415 (1982) is separated the cholesterol in the Wool wax alcohol with U.S. Pat 4977243 (1990) employing column chromatographies, silica gel etc. are made sorbent material, heptane-acetone etc. are made eluent, column temperature is that room temperature to 60 ℃ is carried out wash-out, can obtain the thick cholesterol more than 67%, through the cholesteric purity of recrystallization more than 90%.Chinese patent CN 1958596A adopts silica gel or γ-activated alumina or macroporous adsorbent resin to make adsorption medium, and the mixture of sherwood oil and toluene is made eluent and carried out wash-out, can obtain the cholesterol crude product of content～90%.The cholesterol purity height that chromatography obtains, but solvent consumption is big, treatment capacity is little, and this method is limited to small-scale production.
Reported among the Chinese patent CN 101074257A that the supercutical fluid method is applied to cholesteric separation and Extraction in the lanosterol, make entrainment agent with lower alcohols, acetone and hexane etc., extracting pressure 12～40MPa, 40～80 ℃ of extraction temperature, extraction time 120～480min, the extraction kettle resistates is cholesteric enriched material, obtains the cholesterol of 90% above content through recrystallization.The flow process of this method is short, do not need a large amount of organic solvents, but the investment of supercutical fluid equipment is big, the process cost height.
The character of the high fatty alcohol that contains in the Wool wax alcohol, sterol and triterpene alcohol is very similar, therefore adopts a kind of method to be difficult to therefrom obtain highly purified natural cholesterol.And the high fatty alcohol in the Wool wax alcohol, lanosterol etc. also have certain industrial use, how to realize that the comprehensive utilization of various alcohols materials is significant to industrial production.
Summary of the invention
The object of the invention provide a kind of environmentally friendly and be easy to industrialized from Wool wax alcohol the cholesteric method of separation and Extraction.
The cholesteric method of Wool wax alcohol production high purity of the present invention is to utilize molecular distillation technique refined wool fat alcohol, re-uses the solvent selectivity crystallization method and obtains lanosterol and highly purified cholesterol respectively.
Technical solution of the present invention is:
With molecular distillation separation industries level Wool wax alcohol (cholesterol content 6.5～10.5%), process substep selective crystallization obtains the crude lanosterol product and the cholesterol of purity more than 90% of content 63～70% respectively, and concrete technical process is as follows:
(1) Wool wax alcohol is carried out molecular distillation, collecting light phase cut is refined wool fat alcohol, 160～200 ℃ of vaporization temperatures, feeding rate reaches 2～6ml/min, and the knifing rotating speed reaches 200～300rpm, vacuum tightness 0.1～5Pa, the condensing surface temperature is 50～70 ℃, 60～80 ℃ of preheating temperatures;
(2) the refined wool fat alcohol that molecular distillation is obtained is heated to dissolving fully in the mixed solvent of being made of methyl alcohol and acetone, be cooled to cooling temperature then, and be incubated 6～12h, the vacuum filtration of suspension process obtains the by product crude lanosterol product of white needles, and filtrate is cholesteric preliminary enriched material through the residuum after the underpressure distillation;
(3) with cholesteric preliminary enriched material heating for dissolving in acetone, cooling is separated out and is filtered, and filtrate is through vacuum distillation recovered solvent, and residuum is cholesteric secondary concentration thing;
(4) with cholesteric secondary concentration thing heating for dissolving in alcoholic solvent, be incubated 6～12h after being cooled to cooling temperature, vacuum filtration obtains the cholesterol crude product of white needles; The cholesterol crude product obtains refined cholesterol product through the methanol-acetone mixed solvent recrystallization.
The percent by volume of methyl alcohol is 50～100% in the mixed solvent of being made up of methyl alcohol and acetone of described step (2), and refined wool fat alcohol is 1: 16～30 with the mass ratio of mixed solvent, 10～20 ℃ of cooling temperatures.Described methyl alcohol percent by volume is preferably 60～80%, and refined wool fat alcohol is preferably 1: 18 with the mass ratio of mixed solvent～and 20, cooling temperature is preferably 15～20 ℃.
The cholesteric preliminary enriched material in the described step (3) and the mass ratio of acetone are 1: 5～8, are cooled to 18～22 ℃.
Alcoholic solvent in the described step (4) is an ethanol, the mass ratio 1: 3～7 of cholesteric secondary concentration thing and alcoholic solvent, 10～25 ℃ of cooling temperatures.The mass ratio of cholesteric secondary concentration thing and alcoholic solvent is preferably 1: 4～and 6, cooling temperature is preferably 15～20 ℃.
The refined cholesterol product that cholesterol standard substance and this paper make is tested with infrared spectroscopy, as depicted in figs. 1 and 2.The infrared principal character of cholesterol standard substance is absorbed with: the stretching vibration v of hydroxyl
OH3401cm
-1, the stretching vibration v of saturated carbon hydrogen bond
-CH2934cm
-1And 2867cm
-1, the stretching vibration v of carbon-carbon double bond
C-C1638cm
-1, the flexural vibration δ of saturated carbon hydrogen bond
-CH1465 and 1378cm
-1, the stretching vibration v of carbon-oxygen bond
C-O1056cm
-1, the flexural vibration δ of trans disubstituted olefin
=CH956cm
-1δ with three substituted olefines
=CH839cm
-1Each characteristic infrared absorption spike numerical value in the infrared spectrogram of the refined cholesterol of this experiment conforms to the cholesterol standard sample spectrum.
Cholesteric separating and extracting method has the following advantages in the Wool wax alcohol of the present invention:
1. the present invention directly uses the physical method for separation technology to extract cholesterol, has avoided using the chemical adjuvant of chemical process to use many shortcomings such as environmental pollution and component easily go to pot that cause easily.
2. the molecular distillation technique of the present invention's use can not destroy the component of Wool wax alcohol substantially, obtains the lighter color of Wool wax alcohol, and odorless can directly use as refined wool fat alcohol, and help separation operations such as follow-up crystallization, extraction or column chromatography.
3. the present invention can obtain highly purified cholesterol, and by product lanosterol, the present invention has overcome problems such as the technology that chemical process separation and Extraction cholesterol brings is loaded down with trivial details, environmental pollution, solvent can recycle, refined wool fat alcohol has obtained the by product lanosterol of content 63～70% and the cholesterol product of purity more than 90% by the solvent selectivity crystallization; And can obtain common and braid wool sterol byproduct simultaneously.
4. the main component in the raw material has obtained abundant recovery.
5. each kind solvent of crystallisation process can directly be recycled among the present invention, and chemical adjuvant consumption is few, and molecular distillation and crystallization processes are simple to operate, stable, all are easy to realize suitability for industrialized production.
Description of drawings
Fig. 1 is the infrared spectrogram of cholesterol standard specimen;
Fig. 2 is the infrared spectrogram of refined cholesterol.
Embodiment
Below be the specific embodiment of the present invention, described embodiment is for further describing the present invention, rather than restriction the present invention.
[embodiment 1]
Use molecular distillation-solvent selectivity crystallization technique and separate cholesteric method in the Wool wax alcohol, mainly comprise the steps:
1) molecular distillation refined wool fat alcohol: get 50g raw material Wool wax alcohol (cholesteric content 10.5%), enter into the scraped film type molecular distillation apparatus with the speed of 2.0ml/min.The molecular distillation operational condition is: system pressure 0.1Pa, and 60 ℃ of preheating temperatures, 50 ℃ of condensing surface temperature, 160 ℃ of distillation temperatures, knifing rotating speed 200rpm collects the flaxen light phase cut of 28.6g.
2) the light phase cut of molecular distillation is heated to dissolving fully in 858g methyl alcohol, is cooled to 20 ℃ then, insulation 8h final vacuum filters, and obtains the needle-like crystal of 10.29g white, is the crude lanosterol product of content 70%.
3) filtrate step 2) is removed solvent through underpressure distillation and is got residuum 18.4g, and residuum is heating for dissolving in 92g acetone, is incubated 4h after being cooled to 22 ℃, and vacuum filtration gets flaxen wax shape high fatty alcohol 2.6g.
4) distillation of the filtrate decompression in the step 3) is removed solvent and is got the 16.0g residuum, residuum is heated to dissolving fully in 48g ethanol, be cooled to 10 ℃, and insulation 8h, vacuum filtration obtains the cholesterol crude product 3.24g of white needles, this crude product in the mixed solvent of methyl alcohol-acetone behind the recrystallization cholesteric purity more than 90%.
[embodiment 2]
Basic technology is with embodiment 1, and the concrete operations parameter is as follows:
1) molecular distillation refined wool fat alcohol: get 50g raw material Wool wax alcohol (cholesteric content 8.42%), enter into the scraped film type molecular distillation apparatus with the speed of 4.0ml/min.The molecular distillation operational condition is: system pressure 5Pa, and 80 ℃ of preheating temperatures, 70 ℃ of condensing surface temperature, 200 ℃ of distillation temperatures, knifing rotating speed 300rpm collects the flaxen light phase cut of 29.2g.
2) the light phase cut of molecular distillation is heated to dissolving fully in the mixed solvent (the methyl alcohol percent by volume is 50%) that 467.2g is made up of methyl alcohol and acetone, be cooled to 10 ℃ then, insulation 8h final vacuum filters, obtain the needle-like crystal of 11.43g white, be the crude lanosterol product of content 62.95%.
3) filtrate step 2) is removed solvent through underpressure distillation and is got the 17.9g residuum, and residuum is heating for dissolving in 143.2g acetone, is incubated 4h after being cooled to 18 ℃, and vacuum filtration gets flaxen wax shape high fatty alcohol 2.23g.
4) filtrate in the step 3) is removed solvent through underpressure distillation and is got the 15.8g residuum, residuum is heated to dissolving fully in 110.6g ethanol, be cooled to 25 ℃, and insulation 8h, vacuum filtration obtains the cholesterol crude product 2.12g of white needles, this crude product in the mixed solvent of methyl alcohol-acetone behind the recrystallization cholesteric purity more than 90%.
[embodiment 3]
Basic technology is with embodiment 1, and the concrete operations parameter is as follows:
1) molecular distillation refined wool fat alcohol: get 50g raw material Wool wax alcohol (cholesteric content 10.5%), enter into the scraped film type molecular distillation apparatus with the speed of 6.0ml/min.The molecular distillation operational condition is: system pressure 0.4Pa, and 70 ℃ of preheating temperatures, 60 ℃ of condensing surface temperature, 180 ℃ of distillation temperatures, knifing rotating speed 250rpm collects the flaxen light phase cut of 27.4g.
2) the light phase cut of molecular distillation is heated to dissolving fully in the mixed solvent (methyl alcohol percent by volume 80%) that 548g is made up of methyl alcohol and acetone, be cooled to 15 ℃ then, insulation 8h final vacuum filters, and obtains the needle-like crystal of 10.76g white, is the crude lanosterol product of content 67.61%.
3) filtrate step 2) is removed solvent through underpressure distillation and is got the 16.6g residuum, and residuum is heating for dissolving in 100g acetone, is incubated 4h after being cooled to 20 ℃, and vacuum filtration gets flaxen wax shape high fatty alcohol 2.5g.
4) filtrate in the step 3) is removed solvent through underpressure distillation and is got the 14.1g residuum, residuum is heated to dissolving fully in 56.4g ethanol, be cooled to 15 ℃, and insulation 8h, vacuum filtration obtains the cholesterol crude product 3.11g of white needles, this crude product in the mixed solvent of methyl alcohol-acetone behind the recrystallization cholesteric purity more than 90%.
[embodiment 4]
Basic technology is with embodiment 1, and the concrete operations parameter is as follows:
1) molecular distillation refined wool fat alcohol: get 50g raw material Wool wax alcohol (cholesteric content 6.5%), enter into the scraped film type molecular distillation apparatus with the speed of 3.0ml/min.The molecular distillation operational condition is: system pressure 0.2Pa, and 80 ℃ of preheating temperatures, 70 ℃ of condensing surface temperature, 170 ℃ of distillation temperatures, knifing rotating speed 250rpm collects the flaxen light phase cut of 28.6g.
2) the light phase cut of molecular distillation is heated to dissolving fully in the mixed solvent (percent by volume of methyl alcohol is 60%) that 514.8g is made up of methyl alcohol and acetone, be cooled to 12 ℃ then, insulation 8h final vacuum filters, obtain the needle-like crystal of 11.59g white, be the crude lanosterol product of content 63.57%.
3) filtrate step 2) is removed solvent through underpressure distillation and is got the 17.2g residuum, and residuum is heating for dissolving in 103.2g acetone, is incubated 4h after being cooled to 20 ℃, and vacuum filtration gets flaxen wax shape high fatty alcohol 2.27g.
4) filtrate in the step 3) is removed solvent through underpressure distillation and is got the 15.1g residuum, residuum is heated to dissolving fully in 90.6g ethanol, be cooled to 20 ℃, and insulation 8h, vacuum filtration obtains the cholesteric crude product 2.56g of white needles, this crude product in the mixed solvent of methyl alcohol-acetone behind the recrystallization cholesteric purity more than 90%.
[embodiment 5]
Basic technology is with embodiment 1, and the concrete operations parameter is as follows:
1) molecular distillation refined wool fat alcohol: get 50g raw material Wool wax alcohol (cholesteric content 9.4%), enter into the scraped film type molecular distillation apparatus with the speed of 3.0ml/min.The molecular distillation operational condition is: system pressure 3Pa, and 80 ℃ of preheating temperatures, 70 ℃ of condensing surface temperature, 180 ℃ of distillation temperatures, knifing rotating speed 250rpm collects the flaxen light phase cut of 27.8g.
2) the light phase cut of molecular distillation is heated to dissolving fully in the mixed solvent (percent by volume of methyl alcohol is 70%) that 528.2g is made up of methyl alcohol and acetone, be cooled to 18 ℃ then, insulation 8h final vacuum filters, obtain the needle-like crystal of 10.52g white, be the crude lanosterol product of content 65.78%.
3) filtrate step 2) is removed solvent through underpressure distillation and is got the 17.5g residuum, and residuum is heating for dissolving in 113.5g acetone, is incubated 4h after being cooled to 20 ℃, and vacuum filtration gets flaxen wax shape high fatty alcohol 2.06g.
4) filtrate in the step 3) is removed solvent through underpressure distillation and is got the 15.6g residuum, residuum is heated to dissolving fully in 78g ethanol, be cooled to 18 ℃, and insulation 8h, vacuum filtration obtains the cholesteric crude product 2.94g of white needles, this crude product in the mixed solvent of methyl alcohol-acetone behind the recrystallization cholesteric purity more than 90%.
Cholesteric separating and extracting method in the Wool wax alcohol that the present invention proposes, be described by embodiment, person skilled obviously can be changed or suitably change and combination making method as herein described in not breaking away from content of the present invention, spirit and scope, realizes the technology of the present invention.Special needs to be pointed out is, the replacement that all are similar and change apparent to those skilled in the artly, they are regarded as being included in spirit of the present invention, scope and the content.
Claims (6)
1. cholesteric method of separation and Extraction from Wool wax alcohol is characterized in that may further comprise the steps:
(1) Wool wax alcohol is carried out molecular distillation, collecting light phase cut is refined wool fat alcohol, 160～200 ℃ of vaporization temperatures, feeding rate reaches 2～6ml/min, and the knifing rotating speed reaches 200～300rpm, vacuum tightness 0.1～5Pa, the condensing surface temperature is 50～70 ℃, 60～80 ℃ of preheating temperatures;
(2) the refined wool fat alcohol that molecular distillation is obtained is heated to dissolving fully in the mixed solvent of being made of methyl alcohol and acetone, be incubated 6～12h after being cooled to cooling temperature then, the vacuum filtration of suspension process obtains the by product crude lanosterol product of white needles, and filtrate is cholesteric preliminary enriched material through the residuum after the underpressure distillation;
(3) with cholesteric preliminary enriched material heating for dissolving in acetone, cooling is separated out and is filtered, and filtrate is through vacuum distillation recovered solvent, and residuum is cholesteric secondary concentration thing;
(4) with cholesteric secondary concentration thing heating for dissolving in alcoholic solvent, be incubated 6～12h after being cooled to cooling temperature, vacuum filtration obtains the cholesterol crude product of white needles; The cholesterol crude product obtains refined cholesterol product through the methanol-acetone mixed solvent recrystallization.
2. the method for claim 1, the percent by volume that it is characterized in that methyl alcohol in the mixed solvent of being made up of methyl alcohol and acetone of described step (2) is 50～100%, refined wool fat alcohol is 1: 16～30 with the mass ratio of mixed solvent, is cooled to 10～20 ℃.
3. the method described in claim 2 is characterized in that the percent by volume of methyl alcohol in the described mixed solvent of being made up of methyl alcohol and acetone is 60～80%, and the mass ratio 1: 18～20 of refined wool fat alcohol and solvent is cooled to 15～20 ℃.
4. the method for claim 1 is characterized in that the mass ratio of cholesteric preliminary enriched material and solvent acetone is 1: 5～8 in the described step (3), is cooled to 18～22 ℃.
5. the method for claim 1 is characterized in that the alcoholic solvent in the described step (4) is an ethanol, and the mass ratio 1: 3～7 of cholesteric secondary concentration thing and alcoholic solvent is cooled to 10～25 ℃.
6. method as claimed in claim 5 is characterized in that the mass ratio of described cholesteric secondary concentration thing and alcoholic solvent is 1: 4～6, is cooled to 15～20 ℃.
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617687A (en) * | 2012-03-07 | 2012-08-01 | 南京工业大学 | Process for preparing high-purity cholesterol |
| CN102676626A (en) * | 2012-05-24 | 2012-09-19 | 河南利伟生物药业股份有限公司 | Method for preparing cholesterol by microbial conversion method |
| CN103102380A (en) * | 2013-02-25 | 2013-05-15 | 上海艾韦特医药科技有限公司 | Production method of high purity lanolin cholesterol |
| CN103113446A (en) * | 2013-03-15 | 2013-05-22 | 北京化工大学 | Method for separating and extracting sterol from wool fat |
| CN103554207A (en) * | 2013-10-30 | 2014-02-05 | 吉安荣威生物科技有限公司 | Lanolin cholesterol production technology |
| CN103626820A (en) * | 2013-10-25 | 2014-03-12 | 杭州下沙生物科技有限公司 | Method for preparing high-purity lanolin cholesterol |
| 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 |
| CN110684070A (en) * | 2019-10-30 | 2020-01-14 | 南宁学院 | Method for extracting cholesterol from beef tripe |
| CN111171098A (en) * | 2020-01-14 | 2020-05-19 | 江西天新药业股份有限公司 | Method for preparing cholesterol by using lanolin |
| CN113663599A (en) * | 2021-08-19 | 2021-11-19 | 浙江花园营养科技有限公司 | Method for preparing micro-particle medical grade lanonol |
| 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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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617687A (en) * | 2012-03-07 | 2012-08-01 | 南京工业大学 | Process for preparing high-purity cholesterol |
| CN102676626A (en) * | 2012-05-24 | 2012-09-19 | 河南利伟生物药业股份有限公司 | Method for preparing cholesterol by microbial conversion method |
| CN103102380A (en) * | 2013-02-25 | 2013-05-15 | 上海艾韦特医药科技有限公司 | Production method of high purity lanolin cholesterol |
| CN103102380B (en) * | 2013-02-25 | 2015-04-22 | 上海艾韦特医药科技有限公司 | Production method of high purity lanolin cholesterol |
| CN103113446B (en) * | 2013-03-15 | 2015-11-18 | 北京化工大学 | The method of separation and Extraction sterol from lanolin |
| CN103113446A (en) * | 2013-03-15 | 2013-05-22 | 北京化工大学 | Method for separating and extracting sterol from wool fat |
| CN103626820A (en) * | 2013-10-25 | 2014-03-12 | 杭州下沙生物科技有限公司 | Method for preparing high-purity lanolin cholesterol |
| CN103626820B (en) * | 2013-10-25 | 2015-08-19 | 杭州下沙生物科技有限公司 | A kind of high purity lanolin cholesterol preparation method |
| CN103554207A (en) * | 2013-10-30 | 2014-02-05 | 吉安荣威生物科技有限公司 | Lanolin cholesterol production technology |
| 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 |
| CN110684070A (en) * | 2019-10-30 | 2020-01-14 | 南宁学院 | Method for extracting cholesterol from beef tripe |
| CN111171098A (en) * | 2020-01-14 | 2020-05-19 | 江西天新药业股份有限公司 | Method for preparing cholesterol by using lanolin |
| CN113663599A (en) * | 2021-08-19 | 2021-11-19 | 浙江花园营养科技有限公司 | Method for preparing micro-particle medical grade lanonol |
| 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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| CN101817859B (en) | 2012-07-18 |
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