CN101492339B - Process and apparatus for the extraction separation of beta-elemene, and process for producing stuffing - Google Patents
Process and apparatus for the extraction separation of beta-elemene, and process for producing stuffing Download PDFInfo
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Abstract
The invention relates to a method for extracting and separating beta-elemene, a device thereof and a method for preparing a filling thereof. The method for extracting and separating the beta-elemene provided by the embodiment of the invention comprises the steps as follows: the raw material of the beta-elemene is added to the upper end of a chromatography column, wherein, the chromatography column is provided with silver nitrate surface modification filling; eluent is added into the chromatography column to elute the mixed raw material of the beta-elemene and the filling; solution after the elution is collected at times; and silver ion in the solution which is collected at times after the elution is removed. In addition, the embodiment of the invention also provides the device used for extracting and separating the beta-elemene and the method for preparing the silver nitrate surface modification filling which is used in the method for extracting and separating the beta-elemene.
Description
Technical field
The present invention relates to the extraction and separation technology of beta-elemene, particularly relate to a kind of extraction and separation method and extraction separation device thereof of beta-elemene, and the preparation method of Silver Nitrate modified filler who is used for the extraction and separation method of above-mentioned beta-elemene.
Background technology
Elemenum is separated from zedoary turmeric oil, pamorusa oil, now has been widely used in the treatment cancer.The cancer therapy drug of Ying Yonging is to make Oleum Curcumae injection with zedoary turmeric oil the earliest, this injection liquid can only be treated cervical cancer with the mode of taking the administration of local knurl body, its course of treatment, long, administration operation inconvenience then can't adopt this injection liquid effectively to treat for other various cancers.Use circumscribed problem in order to solve Oleum Curcumae injection, people will have the Elemenum of fixed mixing ratio composition and separate from zedoary turmeric oil, pamorusa oil, make elemene injection.Elemene injection except that can the administration of local knurl body, the regional administration, but also intravenous injection can be treated multiple cancers such as cervical cancer, brain tumor, malignant tumor of digestive tract, malignant pleural effusion, malignant abdominal cavity effusion and leukemia, clinical application range is wider.
The main effective constituent of Elemenum performance antitumor action be beta-elemene (β-elemenum), its chemical name be (1S, 2S, 4R) 1-methyl isophthalic acid-vinyl-2,4-di-isopropyl hexanaphthene, molecular weight are 204.Below be the structural formula of beta-elemene:
The content of beta-elemene what directly have influence on the quality of therapeutic action, so people are at the extraction and separation method of exploring beta-elemene, to prepare the high density beta-elemene.
Patent publication No. is that the patent application of CN101229989A discloses a kind of method for preparing the high density beta-elemene, it carries out underpressure distillation earlier by beta-elemene content being not more than 5% pamorusa oil by product, and then carry out high vacuum rectification, to obtain content at 95.0%～99.9% beta-elemene.But this extraction and separation method relates to underpressure distillation and high vacuum rectification to be handled, and easily causes the generation of beta-elemene oxidizing reaction, thereby makes complex process, preparation cost height, disposable separation efficiency low.
Therefore, in the extraction and separation process of beta-elemene, in order to solve this extraction and separation process complexity, preparation cost height, technical problem that disposable separation efficiency is low, need to seek a kind of beta-elemene extraction and separation method that underpressure distillation combines with high vacuum rectification that is different from.
Summary of the invention
In view of this, the invention provides a kind of extraction and separation method and device and filler preparation method of beta-elemene.Extraction and separation method that the present invention uses and extraction separation device can be simplified beta-elemene preparation technology, reduce preparation cost, improve disposable separation efficiency.
For achieving the above object, the invention provides a kind of extraction and separation method of beta-elemene, this method comprises the steps:
Get the beta-elemene raw material and join the chromatography column upper end, be equipped with the Silver Nitrate surface modifying stuffing in the wherein said chromatography column;
Get eluent and join described chromatography column upper end, described beta-elemene raw material of blended and described filler are carried out wash-out;
The solution behind the wash-out is collected in timesharing, removes the silver ions in the solution behind the wash-out that timesharing collects.
The embodiment of the invention also provides a kind of extraction separation device that is used for the extraction and separation method of beta-elemene, the extraction separation device of this beta-elemene comprises: the beta-elemene raw material that is positioned at described extraction separation device upper end adds inlet and eluent adds inlet, be positioned at that described raw material adds inlet and eluent adds the filler filling portion of the bottom that enters the mouth, and the elute soln outlet that is positioned at described extraction separation device lower end, be filled with the Silver Nitrate surface modifying stuffing in the wherein said filler filling portion.
In addition, the present invention also provides a kind of preparation method of Silver Nitrate surface modifying stuffing of the extraction and separation method that is used for above-mentioned beta-elemene, and this preparation method comprises following step:
It is in 50～90% the methanol aqueous solution that Silver Nitrate is dissolved in the methyl alcohol volume ratio;
Add filler and mix, the weight of wherein said Silver Nitrate is 10%～15% of filler weight;
Lucifuge is soaked described filler that mixes and methanol aqueous solution, and the decompression rotary evaporation is dried the filler of preparing the Silver Nitrate surface modification to the flowing powder shape down in 100 ℃～120 ℃.
Technique scheme of the present invention is based on such principle: contain two key unsaturated compounds and can react with Silver Nitrate and produce 'Pi ' complex compounds, and under certain conditions, the 'Pi ' complex compounds unsaturated compound that can oppositely dissociate, and free speed and unsaturated double-bond what and sterically hindered relevant.The beta-elemene raw material can react with the filler of Silver Nitrate surface modification and produce 'Pi ' complex compounds, and beta-elemene can dissociate from described 'Pi ' complex compounds, and beta-elemene is compared its speed of dissociating out with other impurity variant, thereby make that the beta-elemene in the beta-elemene raw material can not eluted with other impurity simultaneously together when wash-out, thereby can reach the purpose of isolating beta-elemene.In embodiments of the present invention, owing to used filler and the beta-elemene of Silver Nitrate modification to react, thus the beta-elemene extraction and separation process of having avoided underpressure distillation to combine with high vacuum rectification, thus the cost that technology, reduction prepare can be simplified.
Because in technical scheme of the present invention, only be that filler by using the Silver Nitrate modification just can be separated the beta-elemene in the beta-elemene raw material is disposable, and this disposable isolating efficient height, do not need to carry out complicated separating for several times step, and guaranteed to obtain the beta-elemene of high density simultaneously, reached better technical effect.
Description of drawings
Fig. 1 is the schema of beta-elemene extraction and separation method in the embodiment of the invention one;
Fig. 2 for the wash-out of removing timesharing in the embodiment of the invention one and collecting after the particular flow sheet of silver ions step in the solution;
Fig. 3 is the structural representation of beta-elemene extraction separation device in the embodiment of the invention three;
Fig. 4 is preparation method's schema of the Silver Nitrate surface modifying stuffing in the embodiment of the invention one.
Embodiment
In the prior art,, typically use underpressure distillation and the high vacuum rectification treatment process combines, the pamorusa oil byproduct of low beta-elemene concentration is processed in order to obtain the beta-elemene of high density.Owing to will use underpressure distillation and high vacuum rectification to handle this two kinds of processing means, make complete processing complexity, preparation cost height, disposable separation efficiency low, influenced the preparation efficiency of the beta-elemene of high density.
Therefore, the invention provides a kind of extraction and separation method and extraction separation device and the preparation method who is used for the Silver Nitrate surface modifying stuffing of this extraction and separation method of beta-elemene.Can realize a kind of beta-elemene extraction and separation method that underpressure distillation combines with high vacuum rectification that is different from according to the present invention, simplify beta-elemene preparation technology, reduced preparation cost, improved the disposable separation efficiency of beta-elemene, and guaranteed to obtain the beta-elemene of high density simultaneously.
In an embodiment of the present invention, structural formula by above-mentioned beta-elemene as can be known, beta-elemene is the apolar substance that contains three unsaturated double-bonds, so utilization contains the unsaturated compound of πDian Zi and the process of silver ions formation 'Pi ' complex compounds is this characteristic of reversible, beta-elemene extraction separation from the raw mix of beta-elemene can be come out.Further, the stability of 'Pi ' complex compounds is relevant with unsaturated double-bond and spatial configuration of molecules steric hindrance, when carrying out the wash-out operation, beta-elemene and other Elemene vinyl sesquiterpene material are (for example, α-Elemenum, γ-Elemenum, δ-Elemenum) compare, it is slower than other Elemene vinyl sesquiterpene material by the speed that wash-out comes out, can do not eluted together, so just can be guaranteed from the raw mix of beta-elemene, to extract the beta-elemene that obtains high density along with other Elemene vinyl sesquiterpene material.
Below in conjunction with accompanying drawing specific embodiments of the invention are further described, but the present invention is not limited to following embodiment.In an embodiment of the present invention, identical label has been represented identical or similar step or device.
Referring to Fig. 1, Fig. 1 is the schema of beta-elemene extraction and separation method in the embodiment of the invention one, and it includes following step:
Step 101: get the beta-elemene raw material and join the chromatography column upper end, be equipped with the filler of Silver Nitrate surface modification in the wherein said chromatography column;
In this embodiment, described filler can be silica gel, gac or aluminum oxide, and it is filled in the described chromatography column, is used for reacting with the beta-elemene raw material that joins chromatography column.Wherein, because beta-elemene belongs to unsaturated compound, it can react with the Silver Nitrate in the filler of Silver Nitrate surface modification, and generates 'Pi ' complex compounds, and this reaction is a reversible.It among the present invention the reversibility of utilizing this reaction, by eluent the 'Pi ' complex compounds of above-mentioned generation is carried out wash-out, and then than other Elemene vinyl sesquiterpene material (for example according to beta-elemene, α-Elemenum, γ-Elemenum, δ-Elemenum) speed of being come out by wash-out wants slow this characteristic, can be with the beta-elemene that contains silver ions in section centralized collection sometime, and then break away to fall the beta-elemene that silver ions obtains high density.
In the present embodiment, described beta-elemene raw material can be lemongrass time oil.
Step 102: get eluent and join described chromatography column upper end, described beta-elemene raw material of blended and described filler are carried out wash-out;
In this embodiment, after having added the beta-elemene raw material and described filler mixed, add eluent blended beta-elemene raw material and described filler are carried out wash-out, wherein eluent can be sherwood oil, normal hexane, ethyl acetate, methyl alcohol or the above-mentioned substance solvent according to the combination of different volumes ratio.
In the prior art, the generation coordination compound because beta-elemene does not react, therefore when eluent carried out wash-out to beta-elemene, eluent and beta-elemene were eluted together, thereby can not realize isolating effect.
But in the present embodiment, according to the above-mentioned 'Pi ' complex compounds and the reversible reaction process of silver ions, described eluent can react with the 'Pi ' complex compounds that the reaction of silver ions and beta-elemene is produced, thereby makes and dissociate beta-elemene in the 'Pi ' complex compounds.And because beta-elemene than other impurity in the beta-elemene raw material (for example, α-Elemenum, γ-Elemenum, δ-Elemenum) speed of dissociating out from 'Pi ' complex compounds wants slow, thereby can be so that beta-elemene is separated from the beta-elemene raw material, thereby make that the purity of the beta-elemene collected is different in the different time periods, by such purpose of separating beta-elemene that just can reach, thus the beta-elemene of acquisition high density.
Preferably, described eluent is the solvent that sherwood oil or normal hexane and ethyl acetate make up in proportion, and wherein the volume ratio of sherwood oil or normal hexane is 50%～100%.
Step 103: the solution behind the wash-out is collected in timesharing, removes the silver ions in the solution behind the wash-out that timesharing collects;
The timed interval that above-mentioned timesharing is collected is preferably 10 minutes, also can adjust according to the concentration of what and the beta-elemene collected of charging, to guarantee to obtain the beta-elemene of high density.
Therefore the part solution that contains beta-elemene can be put together by the solution behind the timesharing collection wash-out, and then behind the wash-out of removing the timesharing collection, behind the silver ions in the solution, can realize obtaining of high density beta-elemene.
In this embodiment, the step of the solution behind the preferably described timesharing collection wash-out comprises:
Adopt vapor-phase chromatography to detect behind the collected wash-out mass ratio of beta-elemene in the solution, and be that solution is collected in together behind the wash-out more than 98% the beta-elemene mass ratio.
As shown in Figure 2, its for the wash-out of removing timesharing in the embodiment of the invention one and collecting after the particular flow sheet of silver ions step in the solution.Describedly remove that the silver ions in the solution comprises following step particularly behind the wash-out that timesharing collects:
Step 201: with solution decompression evaporation behind the wash-out of timesharing collection, and add sherwood oil, place separating funnel;
Preferably, also can be to use normal hexane to substitute sherwood oil here.
Step 202: the sodium chloride solution that adds sodium-chlor mass ratio 10% shakes up the back layering in separating funnel, emit water layer, removes silver ions;
Step 203: the sodium chloride solution that adds sodium-chlor mass ratio 10% then shakes up the back layering in separating funnel, emit petroleum ether layer, carries out reduction vaporization and removes sherwood oil, thereby obtain beta-elemene.
Preferably, when using normal hexane, be exactly to emit the normal hexane layer in the above-mentioned steps, and carry out reduction vaporization and remove normal hexane, thereby obtain beta-elemene.
Separating funnel in the present embodiment can also for example divide flow container for other liquid distributing device of the prior art.
Embodiments of the invention two have disclosed a kind of beta-elemene extraction separation device, it comprises: the beta-elemene raw material that is positioned at described extraction separation device upper end adds inlet and eluent adds inlet, be positioned at that described raw material adds inlet and eluent adds the filler filling portion of the bottom that enters the mouth, and the elute soln outlet that is positioned at described extraction separation device lower end, wherein in described filler filling portion, be filled with the filler of Silver Nitrate surface modification.
Particularly, described beta-elemene raw material adds inlet and eluent and adds to enter the mouth and be positioned at the upper end of extraction separation device, and is respectively applied for beta-elemene raw material and eluent are joined in the extraction separation device.The filler of Silver Nitrate surface modification is filled in the filler filling portion according to the filling mode of routine, so that react with the beta-elemene raw material that adds the inlet adding by the beta-elemene raw material.The beta-elemene raw material adds the inlet injection by the beta-elemene raw material after, add eluent in the extraction separation device of beta-elemene, described beta-elemene raw material of blended and described filler are carried out wash-out, the solution behind the wash-out flows out by the elute soln outlet.
Preferably, the beta-elemene raw material add the inlet be connected with the container for storing liquid of beta-elemene raw material; Eluent adds inlet and is connected with the eluent container for storing liquid; Elute soln outlet is connected with receiving flask so that solution behind the timesharing collection wash-out.Preferably, use the proofing unit of gas-chromatography that wash-out is collected in timesharing after solution carry out the detection of beta-elemene mass ratio so that the beta-elemene mass ratio that detects according to the gas chromatographic detection device comes the solution after wash-out is collected in timesharing.And then, behind the silver ions behind the wash-out of removing described timesharing collection in the solution, can obtain the beta-elemene of high density.The container for storing liquid of the beta-elemene raw material in the present embodiment and eluent container for storing liquid can also be other device for storing liquid in the prior art, for example liquid-storing box, liquid storage kettle etc.; Receiving flask in the present embodiment can also be other collection device in the prior art, for example collection box, holding tank etc.Preferably, add in being connected of inlet and the device for storing liquid of beta-elemene raw material at described beta-elemene raw material, in being connected of the outlet of described elute soln and collection device, and described eluent add enter the mouth with being connected of eluent device for storing liquid in be provided with valve.
Preferably, the filler in the embodiment of the invention two can be silica gel, gac or aluminum oxide.Preferably, eluent in the embodiment of the invention two is can sherwood oil, normal hexane, ethyl acetate, methyl alcohol or its solvent according to the combination of different volumes ratio, wherein the volume ratio of eluent PetroChina Company Limited. ether or normal hexane is 50%～100% o'clock, obtains the efficient height of the beta-elemene of high density.
Referring to Fig. 3, Fig. 3 is the structural representation of beta-elemene extraction separation device in the embodiment of the invention three.As shown in Figure 3, the extraction separation device of beta-elemene comprises: valve 303, valve 304, valve 305, chromatography column 313, valve 306, valve 307, valve 308; Wherein valve 303 as the beta-elemene raw material add the inlet be connected with the container for storing liquid of beta-elemene raw material, in the present embodiment for to be connected with beta-elemene head tank 302; Valve 304 as eluent add the inlet be connected with the eluent container for storing liquid, in the present embodiment for to be connected with eluent jar 301; Valve 305 is used for behind beta-elemene head tank 302 and eluent jar 301 adding nitrogen, draught head between control beta-elemene head tank 302 or eluent jar 301 and the chromatography column 313 makes beta-elemene raw material and eluent can flow in the chromatography column 313 smoothly; Valve 306 is connected chromatography column 313 bottoms, and it is connected respectively with valve 307, valve 308 as elute soln outlet, and the solution behind the wash-out is collected respectively in receiving flask 311 and the receiving flask 312 by valve 307, valve 308; Wherein valve 309 and valve 310 are respectively the opening-closing valves of receiving flask 311 and receiving flask 312.
Particularly, the extraction separation device of above-mentioned beta-elemene realizes that the concrete steps of beta-elemene extraction operation are as follows:
Connecting adding nitrogen path in beta-elemene head tank 302 and the eluent jar 301, is the not oxidized and control eluent flow velocity of silver ions to guarantee chromatography; Valve-off 304, valve 305 are opened valve 303, valve 306, valve 307, make that the Elemenum raw material enters in the chromatography column 313 under nitrogen gas pressure; After an amount of Elemenum raw material joins in the chromatography column 313, valve-off 303, Open valve 304 makes that eluent enters in the chromatography column 313 under nitrogen gas pressure; The Elemenum raw material carries out abundant wash-out in filler in eluent, collecting elutriant in receiving flask 311, after having collected the time of setting, Open valve 308, valve-off 307, Open valve 308, so that begin to collect solution behind the wash-out in receiving flask 312, collection time gone up in the record of the collection solution in the receiving flask 311, take good care of in order to follow-up operation; After receiving flask 312 was collected well, Open valve 307 again successively, and valve-off 308 is to reach the purpose of interleaved collection.
After solution is finished behind a minute bottle, timesharing collection wash-out, detect the mass ratio of the beta-elemene in each receiving flask according to vapor-phase chromatography, and be that solution puts together behind the wash-out more than 98% with beta-elemene mass ratio in the receiving flask, carry out behind the wash-out that step shown in Figure 2 collects timesharing the silver ions in the solution then and get rid of, thereby obtain the beta-elemene of high density.
Referring to Fig. 4, Fig. 4 is preparation method's schema of the Silver Nitrate surface modifying stuffing in the embodiment of the invention, and this method includes following step:
Step 401: it is in 50～90% the methanol aqueous solution that Silver Nitrate is dissolved in the methyl alcohol volume ratio;
Preferably, the methyl alcohol volume ratio in the methanol aqueous solution described in the step 401 is 70%.
Step 402: add filler and mix, the weight of wherein said Silver Nitrate is 10%～15% of filler weight;
Step 403: lucifuge is soaked 24 hours described fillers that mix and methanol aqueous solution, and the decompression rotary evaporation is to the flowing powder shape, in 120 ℃ down oven dry prepared described filler in 16 hours.
By the above-mentioned embodiment of the invention as can be known, because beta-elemene can produce 'Pi ' complex compounds with Silver Nitrate, make that the beta-elemene in the beta-elemene raw material can not eluted together with other impurity when wash-out, but the beta-elemene that can from described 'Pi ' complex compounds, dissociate, thereby reach isolating purpose.By the embodiment of the invention as can be known, owing to used filler and the beta-elemene of Silver Nitrate modification to react, thus the beta-elemene extraction and separation process of having avoided underpressure distillation to combine with high vacuum rectification, thus the cost that technology, reduction prepare can be simplified.In addition, in an embodiment of the present invention, only be that filler by using the Silver Nitrate modification just can be separated the beta-elemene in the beta-elemene raw material is disposable, and this disposable isolating efficient height, do not need to carry out complicated separating for several times step, and guaranteed to obtain the beta-elemene of high density simultaneously.The mass ratio of the beta-elemene that obtains according to the method in the embodiment of the invention can reach 98%, and the rate of recovery of beta-elemene reaches more than 60%.
The above only is preferred embodiment of the present invention, and is in order to restriction the present invention, within the spirit and principles in the present invention not all, any modification of being made, is equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. preparation method who is used for the Silver Nitrate surface modifying stuffing of beta-elemene extraction separation is characterized in that this preparation method comprises:
It is in 50～90% the methanol aqueous solution that Silver Nitrate is dissolved in the methyl alcohol volume ratio;
Add filler and mix, the weight of wherein said Silver Nitrate is 10%～15% of filler weight;
Lucifuge is soaked described filler that mixes and methanol aqueous solution, and the decompression rotary evaporation is dried the filler of preparing the Silver Nitrate surface modification to the flowing powder shape down in 100 ℃～120 ℃.
2. the extraction and separation method of a beta-elemene is characterized in that, the method comprising the steps of:
Get the beta-elemene raw material and join the chromatography column upper end, be equipped with Silver Nitrate surface modifying stuffing in the wherein said chromatography column via the described preparation method's preparation of claim 1;
Get eluent and join described chromatography column upper end, described beta-elemene raw material of blended and described filler are carried out wash-out;
The solution behind the wash-out is collected in timesharing, removes the silver ions in the solution behind the wash-out that timesharing collects.
3. the extraction and separation method of beta-elemene according to claim 2 is characterized in that, described Silver Nitrate surface modifying stuffing is silica gel, gac or aluminum oxide.
4. the extraction and separation method of beta-elemene according to claim 2 is characterized in that, described eluent is sherwood oil, normal hexane, ethyl acetate, methyl alcohol or the above-mentioned substance solvent according to the combination of different volumes ratio.
5. the extraction and separation method of beta-elemene according to claim 4 is characterized in that, described eluent is the solvent of sherwood oil or normal hexane and ethyl acetate ratio combination by volume, and wherein the volume ratio of sherwood oil or normal hexane is 50%～100%.
6. the extraction and separation method of beta-elemene according to claim 2 is characterized in that, the solution step that described timesharing is collected behind the wash-out is:
Adopting vapor-phase chromatography to detect behind the collected wash-out mass ratio of beta-elemene in the solution, is that solution is collected in together behind the wash-out more than 98% with the beta-elemene mass ratio.
7. the extraction and separation method of beta-elemene according to claim 2 is characterized in that, describedly removes that the silver ions step in the solution is behind the wash-out that timesharing collects:
With solution decompression evaporation behind the wash-out of timesharing collection, and add sherwood oil or normal hexane, place liquid distributing device;
The sodium chloride solution that adds sodium-chlor mass ratio 10% shakes up the back layering in liquid distributing device, emit water layer, removes silver ions;
The sodium chloride solution that adds sodium-chlor mass ratio 10% then shakes up the back layering in liquid distributing device, emit petroleum ether layer or normal hexane layer, carries out reduction vaporization and removes sherwood oil or normal hexane.
8. extraction separation device that is used for the extraction separation beta-elemene comprises:
The beta-elemene raw material that is positioned at described extraction separation device upper end adds inlet and eluent adds inlet, is positioned at that described raw material adds inlet and eluent adds the filler filling portion of the bottom that enters the mouth, and the elute soln that is positioned at described extraction separation device lower end exports;
It is characterized in that, be filled with Silver Nitrate surface modifying stuffing in the described filler filling portion via the described preparation method's preparation of claim 1.
9. extraction separation device according to claim 8, it is characterized in that, described beta-elemene raw material adds inlet and is connected with the device for storing liquid of beta-elemene raw material, and described eluent adds inlet and is connected with the eluent device for storing liquid, and described elute soln outlet is connected with collection device.
10. extraction separation device according to claim 9, it is characterized in that, add in being connected of inlet and the device for storing liquid of beta-elemene raw material at described beta-elemene raw material, in being connected of the outlet of described elute soln and collection device, and described eluent add enter the mouth with being connected of eluent device for storing liquid in be provided with valve.
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| CN101531563A (en) * | 2009-02-16 | 2009-09-16 | 沈阳万爱普利德医药科技有限公司 | Chemical complexing directional separation and purification method for preparing high-purity beta-elemene raw material medicament |
| CN102550892B (en) * | 2010-12-08 | 2013-06-12 | 宏芳香料（昆山）有限公司 | Solvent removing equipment and solvent removing method |
| CN104262076B (en) * | 2014-09-04 | 2016-04-13 | 宁波大红鹰生物工程股份有限公司 | A kind of method utilizing Silver Nitrate silica gel chromatography purification plant origin squalene |
| CN106995361B (en) * | 2017-04-05 | 2019-06-14 | 浙江工业大学 | A method of the separating beta-elemene from oil of zedoary turmeric |
| CN110903156A (en) * | 2019-11-18 | 2020-03-24 | 贵州景诚制药有限公司 | Method for separating and purifying β -elemene, gamma-elemene and delta-elemene |
| CN113717021A (en) * | 2021-10-09 | 2021-11-30 | 山东省分析测试中心 | Method for preparing high-purity sesquiterpene component based on coordination effect and application thereof |
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| CN1554331A (en) * | 2003-12-23 | 2004-12-15 | 英属维尔京群岛远大国际有限公司 | High nurity beta-elemene medicine and its preparing method |
| CN1651366A (en) * | 2004-11-30 | 2005-08-10 | 河北科技大学 | Method of extracting elemene in curcuma zedoary by super critical carbon dioxide fluid extraction-rectification |
| CN1887831A (en) * | 2006-07-21 | 2007-01-03 | 浙江理工大学 | Process of obtaining element |
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| CN1554331A (en) * | 2003-12-23 | 2004-12-15 | 英属维尔京群岛远大国际有限公司 | High nurity beta-elemene medicine and its preparing method |
| CN1651366A (en) * | 2004-11-30 | 2005-08-10 | 河北科技大学 | Method of extracting elemene in curcuma zedoary by super critical carbon dioxide fluid extraction-rectification |
| CN1887831A (en) * | 2006-07-21 | 2007-01-03 | 浙江理工大学 | Process of obtaining element |
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