CN1587251A - Process for preparing chicoric acid from echinacea purpurea - Google Patents
Process for preparing chicoric acid from echinacea purpurea Download PDFInfo
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- CN1587251A CN1587251A CN 200410069076 CN200410069076A CN1587251A CN 1587251 A CN1587251 A CN 1587251A CN 200410069076 CN200410069076 CN 200410069076 CN 200410069076 A CN200410069076 A CN 200410069076A CN 1587251 A CN1587251 A CN 1587251A
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- chicoric acid
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- ethyl acetate
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Abstract
The process of preparing chicoric acid from echinacea purpurea includes organic solvent extraction, acidification, solvent extraction, resin separation, crystal in solvent and other technological steps. During organic solvent extraction, water solution of ethanol of 30-50 wt% concentration and in the amount of 4-10 times echinacea purpurea weight is used as the organic solvent to prepare water solution of chicoric acid at the temperature of 70-90 deg.c. During the acidification of water solution of chicoric acid, the pH value of the water solution of chicoric acid is regulated with acid solution to not greater than 3. The separation and purification process includes separation with macroporous resin, washing with deionized water, elution with ethanol aqua, concentration to obtain coarse chicoric acid product, dissolving the coarse chicoric acid product in water, pH regulation of the chicoric acid aqua to 1-3 and cooling to crystallize and to obtain chicoric acid product with purity over 96 %.
Description
Technical field
The present invention relates to prepare the method for chicoric acid from echinacea purpurea.Be a kind of be raw material with the echinacea purpurea, prepare the method for high pure chicoric acid through technological processs such as organic solvent extraction, acidifying, solvent extraction, resin isolation, solvent crystallizations.
Background technology
Echinacea purpurea (Echinacea purpurea) is a kind of immunopotentiating agent and the immunomodulator that the present world is subjected to generally paying attention to, and its extract and preparation are subjected to greatly paying close attention to both at home and abroad.Echinacea purpurea is successfully introduced a fine variety in China at present.Chicoric acid is the coffic acid derivative, is one of immune active ingredient very important in the echinacea purpurea, has physiological functions such as improving immunizing power, suppress HIV virus, be antiviral.
General in the market sell just as the crude extract of the echinacea purpurea of medicine or healthy food material, chicoric acid content low (1%～4%).People such as Nigel B.Perry are at " Glennie.Echinaceastandardization:analytical methods for phenolic compounds and typical levelsin medicinal species. " (J.Agric.Food Chem, 2001,49 (4): 1702-1706) report can prepare chicoric acid purity greater than 95% method, this method is with chloroform exsiccant echinacea purpurea root material 100g to be carried out pre-treatment, use methanol extraction 24h then, xanchromatic jelly 10g will be obtained behind the methanol extract rotary evaporation in vacuo that obtain, again jelly is dissolved in concentration and is in 1% the aqueous formic acid, with ethyl acetate extraction three times, acetic acid ethyl fluid converges, vacuum-evaporation obtains jelly 2g, with this material by preparation type reverse-phase chromatography column purification, obtain canescence chicoric acid product, purity reaches more than 95%.The preparative chromatography condition is: Merck LichroCart C
18Post; Moving phase 4mL/min; Water: acetonitrile (0.1% formic acid)=7: 3.This method has been used environment and human body harmful's chloroform, methyl alcohol, and the chicoric acid product purity that obtains is not high enough, and preparative scale chromatography costs an arm and a leg, and the moving phase acetonitrile also has severe toxicity except that costing an arm and a leg.People such as Chen Bo are in " high performance liquid chromatography prepares the research of chicoric acid standard reference material " (practical preventive medicine, 2001,8 (1): 15-17) carried out the research that high performance liquid chromatography prepares the chicoric acid reference substance, method is: the echinacea purpurea alcohol extract is made the aqueous solution → static membrane sepn → alcohol precipitation → HPLC and is separated preparation → Concentrated and crystallized in vacuum → purity detecting → product.This method products obtained therefrom purity is greater than 99%, and the preparation yield is greater than 80%.The preparative chromatography condition is Waters Prep-Symmetry C
1810 μ m; 7.8mmID * 150mm; Moving phase: 0.02mol/L NH
4The Ac aqueous solution+methyl alcohol=1000+15 (V+V); Flow velocity: 4mL/min.This method is used expensive preparative liquid chromatography and expensive chromatorgaphy reagent, and cost is very high, only can prepare a spot of witloof acidity scale product, unsuitable scale operation.
Summary of the invention
The object of the present invention is to provide a kind of is the method that raw material is applicable to the highly purified lettuce chrysanthemumic acid of industrial preparation with the echinacea purpurea.It is raw material that the present invention adopts with the echinacea purpurea, prepares highly purified chicoric acid through technological processs such as organic solvent extraction, acidifying, solvent extraction, resin isolation, solvent crystallizations, is suitable for suitability for industrialized production.
The method that prior art prepares chicoric acid from echinacea purpurea is to be raw material through following process with the echinacea purpurea powder: (1) organic solvent extraction prepares the chicoric acid aqueous solution; (2) ethyl acetate extraction, the concentrated chicoric acid medicinal extract that obtains; (3) separate purification; Obtain the chicoric acid product at last.Technical characterictic of the present invention is:
(1) in the organic solvent extraction process:
(A) adopt aqueous ethanolic solution to prepare the chicoric acid aqueous solution as organic solvent extraction, the mass concentration of aqueous ethanolic solution is 30～50%, and the solid-to-liquid ratio of echinacea purpurea and ethanolic soln is 1: 4～10, and extracting temperature is 70～90 ℃;
(B) the chicoric acid aqueous solution is carried out acidification, regulate pH≤3 of the chicoric acid aqueous solution with acid solution;
(2) in separating purification process:
(A) adopt macroporous adsorbent resin to separate, use deionized water wash, the aqueous ethanolic solution wash-out concentrates and obtains the thick product of chicoric acid;
(B) the thick product of chicoric acid is soluble in water, with pH=1～3 of the acid solution adjusting chicoric acid aqueous solution, obtain the smart product of chicoric acid through crystallisation by cooling.
The present invention when ethyl acetate extraction, to by (1) of top process (A) in the chicoric acid aqueous solution of preparation obtain clear liquid and throw out after separating, clear liquid obtains acetic acid ethyl acetate extract with the equal-volume ethyl acetate extraction; Throw out obtains acetic acid ethyl acetate extract with ethyl acetate extraction dissolving, and the consumption of ethyl acetate is according to the solid-to-liquid ratio of echinacea purpurea and ethyl acetate 2: 5; Combined ethyl acetate extraction liquid and acetic acid ethyl acetate extract.
It is styrene tyle macroporous adsorption resin that the present invention separates the macroporous adsorbent resin that adopts of purifying.
The present invention separates that purify to adopt concentration be 10～50% aqueous ethanolic solution.
The present invention is in the solvent crystallization process, and with soluble in water, the mass volume ratio m/v scope of thick product of lettuce acid and water is dissolved under 80～95 ℃ of temperature 3/15～3/5 with the thick product of chicoric acid.
It is HCl, H that the present invention regulates the acid that pH uses
2SO
4Or HNO
3The equivalent concentration of acid preferably is no more than 6N.
The solid-to-liquid ratio that more than relates to, mass volume ratio all are present technique field method for expressing commonly used, and solid-to-liquid ratio refers to the ratio of the volume L of the quality kg of solids component and liquid component.Mass volume ratio m/v refers to the ratio of the volume L of the quality kg of solids component and liquid component.
Echinacea purpurea root and the over-ground part of echinacea purpurea raw material for drying that the present invention is used, the echinacea purpurea over-ground part comprises stem, leaf, flower.The chicoric acid mass content can obtain purity at the smart product of the chicoric acid more than 96% 0.6～2.1% through method of the present invention in the exsiccant echinacea purpurea root raw material.
Specific operation process is as follows:
(1) with after the echinacea purpurea pulverizing of doing, extracts the solution that obtains containing chicoric acid with aqueous ethanolic solution.
(2) above-mentioned solution is removed wherein ethanol through vacuum-evaporation, and concentrate and obtain the spissated chicoric acid aqueous solution.
(3) transfer pH to be less than or equal to 3 with dilute acid soln the above-mentioned chicoric acid aqueous solution.
(4) filtration or centrifugal solid-liquid separate, and obtain clear liquid and throw out after the separation respectively.Clear liquid obtains acetic acid ethyl acetate extract with ethyl acetate extraction; Throw out obtains acetic acid ethyl acetate extract, combined ethyl acetate extraction liquid and acetic acid ethyl acetate extract with the ethyl acetate extraction dissolving.
(5) the amalgamation liquid of above acetic acid ethyl acetate extract that obtains and acetic acid ethyl acetate extract, boil off ethyl acetate, obtain medicinal extract, the spray-dried again chicoric acid product that obtains low-purity with vacuum concentration.
(6) prepare the chicoric acid aqueous solution with water dissolution medicinal extract, use absorption with macroporous adsorbent resin, wash decon with water after, the elutriant that obtains with the aqueous ethanolic solution wash-out is through concentrating the thick product of chicoric acid that obtains higher degree again.
(7) the thick product of chicoric acid is soluble in water, transfer pH to 1～3, crystallisation by cooling with dilute acid soln.Can obtain highly purified chicoric acid product.
Method provided by the invention in the existing method for preparing the lettuce chrysanthemumic acid by different is: adopt aqueous ethanolic solution to make organic solvent in the organic solvent extraction process, increased the acidification process; In separating purification process, adopt macroporous adsorbent resin to separate, increased the solvent crystallization treating processes.
Because chicoric acid solubleness in neutral aqueous solution is big, low with the percentage extraction of ethyl acetate, only have an appointment about 10%.The present invention transfers pH smaller or equal to 3 solution by acidification, and chicoric acid then exists with free form in the aqueous solution, and solubleness reduces in water.Percentage extraction can be brought up to more than 95% during therefore, with ethyl acetate extraction.When regulating the pH of the chicoric acid aqueous solution with acid solution, used acid is diluted acid, and its concentration preferably is no more than equivalent concentration 6N, because of the acid of excessive concentrations can make the sex change of part material, makes that foreign matter content increases in the product.
The present invention separates the styrene tyle macroporous adsorption resin of purifying and adopting, and macroporous adsorbent resins such as the AB-8 of for example commercially available Chemical Plant of Nankai Univ., H103, NAK-2 all can use.The physicals of polymeric adsorbent is as shown in the table:
Resin model particle diameter/mm specific surface area mean pore size
/(m
2/g) /nm
AB-8 0.3～1.25 480～520 13.0～14.0
H103 0.3～1.25 1000～1100 8.5～9.5
NKA-2 0.3～1.25 160～200 14.5～15.5
Method provided by the invention can obtain purity at the chicoric acid product more than 96%.This method technology is simple, adopts aqueous ethanolic solution to make solvent in the organic solvent extraction process, does not use chloroform, methyl alcohol to human body and environmental pollution, does not also use the preparative chromatography and the chromatorgaphy reagent of price lattice costliness; Isolating throw out in the preparation process is also extracted, and increasing operation rate helps further reducing cost.The present invention is suitable for industrial production.
Embodiment
Embodiment 1
(1) organic solvent extraction
50kg echinacea purpurea root powder (chicoric acid content 1.1%) adds 40% the ethanolic soln of 300L, 90 ℃ of refluxing extraction, and extraction time is 3 times, each 2 hours, filter merging filtrate, obtain the aqueous ethanolic solution 850L of chicoric acid, reclaim ethanol, obtain the 120L chicoric acid aqueous solution through concentrating.
(2) acidifying
The chicoric acid aqueous solution that obtains above is that to transfer pH be 3 for the HCl of 6N with equivalent concentration.Solution centrifugal after the acidifying is separated, get clear liquid 115L, and the collecting precipitation thing.
(3) solvent extraction
The ethyl acetate that the 115L clear liquid adds with volume extracts, and extracts three times, and each 2 hours, combining extraction liquid obtained acetic acid ethyl acetate extract.Add the 20L ethyl acetate and stir extraction in throw out, extract 2 times, obtain acetic acid ethyl acetate extract, insolubles discards.Acetic acid ethyl acetate extract and acetic acid ethyl acetate extract merging are obtained medicinal extract through vacuum concentration.It is 1.67 kilograms of 31% chicoric acids that medicinal extract obtains content through vacuum-drying.
(4) resin isolation
1.67 kilograms of thick products that obtain above are dissolved in the 120L water, cross and filter out insolubles.AB-8 macroporous adsorptive resins on the filtrate (column diameter 10cm, the high 100cm of post, resin loading height 63cm, resin volume 50L).Go up the impurity of absorption with 250L deionized water flush away macroporous absorption tree earlier.Use 400L 10% ethanolic soln wash-out again, elutriant concentrates evaporate to dryness.Obtain the thick product 0.683kg of chicoric acid, purity is 72%.
(5) solvent crystallization
With the thick product of 0.683kg that obtains under 95 ℃ by mass volume ratio: m/v=3/10 adds solvent, being to add the 2.27L deionized water in the thick product of 0.683kg, is that 5% hydrochloric acid accent pH is 1.0 with mass concentration, puts gradually in the water-bath and is chilled to 10 ℃, stir frequently, have crystallization to separate out.Filter to collect crystallization,, obtain purity and be 97% the smart product 479g of white chicoric acid with the water washing crystallization of 10 ℃ of 800mL, vacuum-drying.Crystallization yield is 94.5%.
Embodiment 2
(1) organic solvent extraction
50kg echinacea purpurea root powder (chicoric acid content 1.1%), 50% the ethanolic soln that adds 200L, 70 ℃ of refluxing extraction, extraction time is 3 times, each 2 hours, filters, merging filtrate, obtain the aqueous ethanolic solution 560L of chicoric acid, concentrate and reclaim ethanol, obtain the 105L chicoric acid aqueous solution through concentrating.
(2) acidifying
The chicoric acid aqueous solution that obtains above is with the H of equivalent concentration 6N
2SO
4Transferring pH is 1.Solution centrifugal after the acidifying is separated, get clear liquid 98L, and the collecting precipitation thing.
(3) solvent extraction
The ethyl acetate that the 98L clear liquid adds with volume extracts, and extracts three times, and each 2 hours, combining extraction liquid obtained acetic acid ethyl acetate extract.Add the 20L ethyl acetate and stir extraction in throw out, extract 2 times, obtain acetic acid ethyl acetate extract, insolubles discards.Acetic acid ethyl acetate extract and acetic acid ethyl acetate extract merging are obtained medicinal extract through vacuum concentration.It is 1.55 kilograms of 34% chicoric acid products that medicinal extract can obtain content through vacuum-drying.
(4) resin isolation
1.55 kilograms of products that obtain above are dissolved in the 120L water, cross and filter out insolubles.AB-8 macroporous adsorptive resins on the filtrate (column diameter 10cm, the high 100cm of post, resin loading height 63cm, resin volume 50L).Go up the impurity of absorption with 250L deionized water flush away macroporous absorption tree earlier.Use 200L 50% ethanolic soln wash-out again, elutriant concentrates evaporate to dryness.Obtain the thick product 0.703kg of chicoric acid, purity is 69%.
(5) solvent crystallization
The thick product of 0.703kg that obtains is carried out crystallization with deionization, under 80 ℃, press mass volume ratio: m/v=3/15 in the thick product and add solvent, be to add the 3.5L deionized water in the thick product of 0.703kg, with mass concentration is that to transfer pH be 3.0 for 5% hydrochloric acid, put gradually in the water-bath and be chilled to 10 ℃, stir frequently, have crystallization to separate out.Filter to collect crystallization,, obtain purity and be 98.3% the smart product 450g of white chicoric acid with the water washing crystallization of 5 ℃ of 800mL, vacuum-drying.Crystallization yield is 91.2%.
Embodiment 3
(1) organic solvent extraction
50kg echinacea purpurea root powder (chicoric acid content 1.1%), 30% the ethanolic soln that adds 500L, 70 ℃ of refluxing extraction, extraction time is 3 times, each 2 hours, filters, merging filtrate, obtain the aqueous ethanolic solution 1460L of chicoric acid, concentrate and reclaim ethanol, obtain the 220L chicoric acid aqueous solution through concentrating.
(2) acidifying
The chicoric acid aqueous solution that obtains above is the H of 6N with equivalent concentration
2SO
4Transferring pH is 2.Solution centrifugal after the acidifying is separated, get clear liquid 208L, and the collecting precipitation thing.
(3) solvent extraction
The ethyl acetate that the 208L clear liquid adds with volume extracts, and extracts three times, and each 2 hours, combining extraction liquid obtained acetic acid ethyl acetate extract.Add the 20L ethyl acetate and stir extraction in throw out, extract 2 times, obtain acetic acid ethyl acetate extract, insolubles discards.Acetic acid ethyl acetate extract and acetic acid ethyl acetate extract are merged through vacuum concentration, obtain medicinal extract.It is 1.87 kilograms of 29% chicoric acid products that medicinal extract can obtain content through vacuum-drying.
(4) resin isolation
1.87 kilograms of products that obtain above are dissolved in the 120L water, cross and filter out insolubles.NAK-2 macroporous adsorptive resins on the filtrate (column diameter 10cm, the high 100cm of post, resin loading height 63cm, resin volume 50L).Go up the impurity of absorption with 250L deionized water flush away macroporous absorption tree earlier.Use 300L 30% ethanolic soln wash-out again, elutriant concentrates evaporate to dryness.Obtain the thick product 0.709kg of chicoric acid, purity is 70.3%.
(5) solvent crystallization
The thick product of 0.709kg that obtains is carried out crystallization with deionization, under 80 ℃, press mass volume ratio: m/v=3/5 in the thick product and add solvent, be to add the 1.2L deionized water in the thick product of 0.703kg, with mass concentration is that to transfer pH be 2.0 for 5% hydrochloric acid, put gradually in the water-bath and be chilled to 10 ℃, stir frequently, have crystallization to separate out.Filter to collect crystallization,, obtain purity and be 96.3% the smart product 498g of white chicoric acid with the water washing crystallization of 10 ℃ of 1000mL, vacuum-drying.Crystallization yield is 95.2%.
Claims (7)
1, the method for preparing chicoric acid from echinacea purpurea, be the following process of raw material process with the echinacea purpurea powder: (1) organic solvent extraction prepares the chicoric acid aqueous solution; (2) ethyl acetate extraction, the concentrated chicoric acid medicinal extract that obtains; (3) separate purification; Obtain the chicoric acid product at last, it is characterized in that: (1) is in the organic solvent extraction process:
(A) adopt aqueous ethanolic solution to prepare the chicoric acid aqueous solution as organic solvent extraction, the mass concentration of aqueous ethanolic solution is 30～50%, and the solid-to-liquid ratio of echinacea purpurea and ethanolic soln is 1: 4～10, and extracting temperature is 70～90 ℃;
(B) the chicoric acid aqueous solution is carried out acidification, regulate pH≤3 of the chicoric acid aqueous solution with dilute acid soln;
(2) in separating purification process:
(A) adopt macroporous adsorbent resin to separate, use deionized water wash, the aqueous ethanolic solution wash-out concentrates and obtains the thick product of chicoric acid;
(B) with the thick product of chicoric acid with soluble in water, regulate pH=1～3 of the chicoric acid aqueous solution with dilute acid solution, obtain the smart product of chicoric acid through crystallisation by cooling.
2, method according to claim 1, it is characterized in that: when ethyl acetate extraction, obtain clear liquid and throw out after the chicoric acid aqueous solution that (A) is prepared by process (1) separated, clear liquid obtains acetic acid ethyl acetate extract with the equal-volume ethyl acetate extraction; Throw out obtains acetic acid ethyl acetate extract with ethyl acetate extraction dissolving, and the consumption of ethyl acetate is according to the solid-to-liquid ratio of echinacea purpurea and ethyl acetate 2: 5; Combined ethyl acetate extraction liquid and acetic acid ethyl acetate extract.
3, method according to claim 1 is characterized in that: separating the macroporous adsorbent resin that adopts of purifying is styrene tyle macroporous adsorption resin.
4, method according to claim 1 is characterized in that: separation purification employing concentration is 10～50% aqueous ethanolic solution.
5, method according to claim 1 is characterized in that: in the solvent crystallization process that the thick product of chicoric acid is soluble in water, the mass volume ratio m/v scope of thick product of lettuce acid and water is dissolved under 80～95 ℃ of temperature 3/15～3/5.
6, method according to claim 1 is characterized in that: the acid that adjusting pH uses is HCl, H
2SO
4Or HNO
3
7, method according to claim 6 is characterized in that: the equivalent concentration of acid is no more than 6N.
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|---|---|---|---|
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101816693A (en) * | 2010-05-28 | 2010-09-01 | 青岛康地恩药业有限公司 | Echinacea purpurea extract powder and preparation method and application thereof |
| CN101869348A (en) * | 2010-06-25 | 2010-10-27 | 王爱平 | Method for extracting antioxidation active substance from Cichorium endivia L. |
| CN101367728B (en) * | 2008-10-09 | 2010-12-08 | 湖南师范大学 | Method for purifying chicoric acid and monocaffeyltartaric acid from echinacea purpurea extract |
| CN102161620A (en) * | 2011-03-10 | 2011-08-24 | 湖南师范大学 | Method for non column chromatography separation and purification of witloof acid from Echinacea purpurea extractive |
| CN102249917A (en) * | 2011-05-20 | 2011-11-23 | 沈阳双鼎科技有限公司 | Chicoric acid and extraction and separation method and application thereof |
| CN102911056A (en) * | 2012-11-19 | 2013-02-06 | 西安岳达植物科技有限公司 | High-efficiency environment-friendly process for preparing chicoric acid from Echinacea |
| CN105061206A (en) * | 2015-08-19 | 2015-11-18 | 西安岳达植物科技有限公司 | Method for separating chicoric acid from echinacea |
| CN105294440A (en) * | 2015-09-30 | 2016-02-03 | 桂林三宝药业有限公司 | Method for extracting chicoric acid from echinacea purpurea moench |
| CN109867603A (en) * | 2019-04-27 | 2019-06-11 | 蚌埠学院 | A kind of purification process of Cichoric acid |
| CN113845422A (en) * | 2021-11-04 | 2021-12-28 | 山东中医药大学 | Process for preparing high-purity L-chicoric acid from echinacea purpurea in batches and application |
| CN115886126A (en) * | 2022-10-17 | 2023-04-04 | 青海大学 | Chicoric acid feed additive based on plateau environment, preparation method and application |
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2004
- 2004-07-20 CN CN 200410069076 patent/CN1240665C/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367728B (en) * | 2008-10-09 | 2010-12-08 | 湖南师范大学 | Method for purifying chicoric acid and monocaffeyltartaric acid from echinacea purpurea extract |
| CN101816693A (en) * | 2010-05-28 | 2010-09-01 | 青岛康地恩药业有限公司 | Echinacea purpurea extract powder and preparation method and application thereof |
| CN101816693B (en) * | 2010-05-28 | 2011-09-07 | 青岛康地恩药业有限公司 | Echinacea purpurea extract powder and preparation method and application thereof |
| CN101869348A (en) * | 2010-06-25 | 2010-10-27 | 王爱平 | Method for extracting antioxidation active substance from Cichorium endivia L. |
| CN101869348B (en) * | 2010-06-25 | 2013-01-02 | 王爱平 | Method for extracting antioxidation active substance from Cichorium endivia L. |
| CN102161620A (en) * | 2011-03-10 | 2011-08-24 | 湖南师范大学 | Method for non column chromatography separation and purification of witloof acid from Echinacea purpurea extractive |
| CN102161620B (en) * | 2011-03-10 | 2013-01-30 | 湖南师范大学 | Method for non column chromatography separation and purification of witloof acid from Echinacea purpurea extractive |
| CN102249917A (en) * | 2011-05-20 | 2011-11-23 | 沈阳双鼎科技有限公司 | Chicoric acid and extraction and separation method and application thereof |
| CN102911056A (en) * | 2012-11-19 | 2013-02-06 | 西安岳达植物科技有限公司 | High-efficiency environment-friendly process for preparing chicoric acid from Echinacea |
| CN105061206A (en) * | 2015-08-19 | 2015-11-18 | 西安岳达植物科技有限公司 | Method for separating chicoric acid from echinacea |
| CN105294440A (en) * | 2015-09-30 | 2016-02-03 | 桂林三宝药业有限公司 | Method for extracting chicoric acid from echinacea purpurea moench |
| CN109867603A (en) * | 2019-04-27 | 2019-06-11 | 蚌埠学院 | A kind of purification process of Cichoric acid |
| CN109867603B (en) * | 2019-04-27 | 2022-02-22 | 蚌埠学院 | Method for purifying chicoric acid |
| CN113845422A (en) * | 2021-11-04 | 2021-12-28 | 山东中医药大学 | Process for preparing high-purity L-chicoric acid from echinacea purpurea in batches and application |
| CN113845422B (en) * | 2021-11-04 | 2024-01-30 | 山东中医药大学 | Process for preparing L-chicoric acid from Echinacea purpurea in batches and application thereof |
| CN115886126A (en) * | 2022-10-17 | 2023-04-04 | 青海大学 | Chicoric acid feed additive based on plateau environment, preparation method and application |
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