CN101805261A - Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae - Google Patents
Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae Download PDFInfo
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- CN101805261A CN101805261A CN201010135116A CN201010135116A CN101805261A CN 101805261 A CN101805261 A CN 101805261A CN 201010135116 A CN201010135116 A CN 201010135116A CN 201010135116 A CN201010135116 A CN 201010135116A CN 101805261 A CN101805261 A CN 101805261A
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- deionized water
- chlorogenic acid
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- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 title claims abstract description 20
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 title claims abstract description 20
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 title claims abstract description 20
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 title claims abstract description 20
- 229940074393 chlorogenic acid Drugs 0.000 title claims abstract description 20
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 title claims abstract description 20
- 235000001368 chlorogenic acid Nutrition 0.000 title claims abstract description 20
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000002860 competitive effect Effects 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000008367 deionised water Substances 0.000 claims abstract description 17
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 17
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 238000001953 recrystallisation Methods 0.000 claims abstract description 9
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 238000010521 absorption reaction Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 241000208688 Eucommia Species 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 238000005352 clarification Methods 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000002791 soaking Methods 0.000 abstract description 4
- 241000208689 Eucommia ulmoides Species 0.000 abstract description 2
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- 230000003078 antioxidant effect Effects 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract description 2
- 238000004904 shortening Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 235000019439 ethyl acetate Nutrition 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XXLFLUJXWKXUGS-UHFFFAOYSA-N 6-methoxyquinoline-4-carboxylic acid Chemical compound N1=CC=C(C(O)=O)C2=CC(OC)=CC=C21 XXLFLUJXWKXUGS-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000000899 Gutta-Percha Substances 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 240000000342 Palaquium gutta Species 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropyl alcohol Natural products CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002279 cholagogic effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- YTJJRAWFHJBAMT-UHFFFAOYSA-N depside Natural products OC(=O)CC1=C(O)C=C(O)C=C1OC(=O)C1=CC=C(O)C(O)=C1 YTJJRAWFHJBAMT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920000588 gutta-percha Polymers 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- -1 phenylpropyl alcohol chlorins compounds Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing competitive products of chlorogenic acid by folium cortex eucommiae, comprising the technological flows of normal temperature soaking and extraction by adopting deionized water, squeezing (or centrifugalizing), macroporous absorption column chromatography and enrichment, acetic ether extraction and deionized water recrystallization, and taking a series of protective measures aiming at the instability of easy decomposition of target product chlorogenic acid, such as controlling temperature and pH value, adding antioxidant, shortening production cycle and the like. The method has the characteristics of low cost, easy operation, high recovery rate and high content, and opens up a new approach for factorial large-scale development and full utilization of eucommia ulmoides resource.
Description
Technical field
The present invention relates to a kind of method of preparing chlorogenic acid from eucommia leaves elaboration.
Background technology:
The depside that chlorogenic acid (Chlorogenic acid) is made up of coffic acid (Cafieic acid) and quininic acid (Quinic acid), the different name chlorogenic acid, chemical name 3-O-caffeoylquinic acids (3-O-Cafeoylquinic acid), molecular formula is C
16H
18O
9, relative molecular mass 354.30 is a kind of phenylpropyl alcohol chlorins compounds that plant materials produces through shikimic acid pathway in the aerobic repiration process.Chlorogenic acid is a kind of important biological material, have antibiotic, antiviral, increase effects such as white cell, hepatic cholagogic, antitumor, hypotensive, reducing blood-fat, removing free radical and stimulating central nervous system system.It is one of effective constituent of many Chinese medicinal materialss, is again the quality index of some patent medicine.Chlorogenic acid is widely used in industries such as medicine, daily-use chemical industry and food.Though chlorogenic acid is present in all kinds of plants comparatively at large, the higher plant of content is actually rare.Chlorogenic acid contents is higher in studies show that in recent years, the bark of eucommia (Eucommia ulmoides), and the content in its middle period is about 1-3%.As the medicinal history that the centuries has been arranged, cultivated area is quite extensive in China for the bark of eucommia, and the whole nation has 200,000 squares of hectares of bark of eucommia woods approximately, can produce the millions of tons of leaf every year.But the Development and Production of bark of eucommia high-end product lags behind at present, the particularly Separation ﹠ Purification of single component; Low-end product has only fragmentary production, cause the waste of a large amount of eucommia resources, make the condition that faces a difficult selection, the bark of eucommia production base that grows up over, this mainly is because some research only rests on laboratory stage, lack the complete set technology that is applied to actual production, extract medicinal even chemical pure chlorogenic acid if can be used in, will produce huge social and economic benefit undoubtedly.Main extracting method in the Folium Eucommiae chlorogenic acid research at present has: solvent-extraction process, ultrasonic extraction, supercritical CO
2Method, extraction method enzyme extraction method etc.; The method for purifying and separating of chlorogenic acid has: polyamide column chromatography method, ultra-filtration membrane partition method, lead salt precipitation separation, solvent extraction and separation method, macroporous resin partition method.But problems such as aforesaid method exists, and investment is big, technical requirements is high, heavy-metal residual and purity are low, the large-scale production difficulty.
The objective of the invention is to utilize in these years the research basis of chlorogenic acid extraction separation in the Folium Eucommiae, a kind of chlorogenic acid elaboration preparation method with low cost, easy to operate, high-content characteristics is provided.For a new approach is opened up in the development and use of Folium Eucommiae.
---the deionized water soak at room temperature extracts---squeezes (or centrifugal)---column chromatography enrichment---solvent extraction---coarse crystallization---recrystallization (elaboration) in the technical process of preparing chlorogenic acid from eucommia leaves elaboration of the present invention: Folium Eucommiae coarse reduction;
Concrete grammar is as follows:
(1) Folium Eucommiae coarse reduction;
(2) the deionized water soak at room temperature extracts, and temperature 30-40 ℃, regulate pH value to 3.0-3.5, time 30-60 minute/time, repeat 3-4 time,
(3) vat liquor clarification back, adds the reductive agent vacuum and low temperature and concentrates again through the 30-50% ethanol elution with the absorption of macroporous resin upper prop, and wherein macroporous resin is a kind of of AAS, NKA-II, NKA-9, and reductive agent is a kind of of sodium bisulfite, Sulfothiorine,
(4) ethyl acetate extraction elutriant cryoconcentration is to proportion 1.05-1.10, extract with equimultiple water saturation solvent normal temperature, combining extraction liquid, cryoconcentration is to muddy the appearance arranged after reclaiming solvent, leave standstill crystallization, wherein selected extraction solvent is a kind of in propyl carbinol, acetone, the vinyl acetic monomer, also can be its several mixing
(5) recrystallization deionized water 1: 2-1: 4 thermosols, filter stand at low temperature crystallization, cryodrying, finished product.
The present invention adopts the deionized water soak at room temperature to extract; squeezing (or centrifugal); the technical process of the enrichment of macroporous absorption column chromatography, solvent extraction, deionized water recrystallization; taked serial sfgd. at the labile unstable of target product chlorogenic acid: controlled temperature, pH value, adding antioxidant, shortening production cycle etc.; have low-cost, easy to operate, high-recovery and high-load characteristics, for the batch production scale development, make full use of eucommia resource and open up a new approach.
Embodiment
Below in conjunction with three embodiment, the invention will be further described.Embodiment 1. Folium Eucommiae 1000Kg, coarse reduction adds in the 8000L deionized water, and 30 ℃ of soaking temperatures drained after 30 minutes, added deionized water 6000L continuation temperature and soaked, and repeated 4 times.Folium Eucommiae after squeezing is soaked, merge soaked extracting solution, add hydrochloric acid by 1: 5 and adjust pH value to 3.0, go up after filtering adsorption column NKA-9, multicolumn is applied mechanically, saturated to adsorbing, doubly measure wash-out with 30% ethanol, elutriant adds 0.5% (W/V) sodium bisulfite, decompression recycling ethanol, low temperature (T≤60 ℃) is concentrated into proportion 1.05, with 3-4 normal temperature extraction of equimultiple water saturation vinyl acetic monomer, merges vinyl acetic monomer and reclaims low temperature behind the solvent (T≤50 ℃) mutually and be concentrated into muddy appearance, left standstill crystallization 12 hours, recrystallization gets white crystals product 6.4Kg, HPLC content: 98.8%.
Embodiment 2. Folium Eucommiae 1500Kg, coarse reduction, add soaking at room temperature in the 12000L deionized water, intermittently stir 30 ℃ of temperature, drain after 40 minutes, add deionized water 9000L continuation temperature and soak, repeat 4 times, the Folium Eucommiae after squeezing is soaked, merge soaked extracting solution, adjust pH value to 3.0 with 1: 5 hydrochloric acid.Go up after filtering adsorption column AAS, multicolumn is applied mechanically, and is saturated to adsorbing, 30% ethanol is doubly measured wash-out, elutriant adds 0.5% (W/V) sodium bisulfite, 0.3% Sulfothiorine, decompression recycling ethanol, and low temperature (T≤60 ℃) is concentrated into proportion 1.06, with 3-4 normal temperature extraction of equimultiple water saturation vinyl acetic monomer, merge vinyl acetic monomer and reclaim low temperature behind the solvent (T≤50 ℃) mutually and be concentrated into muddy the appearance, left standstill crystallization 12 hours, recrystallization, get white crystals product 9Kg, HPLC content: 98.2%.
Embodiment 3. Folium Eucommiae 1000Kg, coarse reduction, add the 8000L deionized water, 40 ℃ of soaking temperatures drained after 30 minutes, adding deionized water 6000L continuation temperature soaks, repeat 4 times, the Folium Eucommiae after squeezing is soaked merges soaked extracting solution, hydrochloric acid was adjusted pH value to 3.0 in 1: 5, go up after filtering adsorption column NKA-II, multicolumn is applied mechanically, and is saturated to adsorbing, 30% ethanol is doubly measured wash-out, elutriant adds 0.4% (W/V) sodium bisulfite, decompression recycling ethanol, and low temperature (T≤60 ℃) is concentrated into proportion 1.10, with 3-4 normal temperature extraction of equimultiple water saturation vinyl acetic monomer, merge vinyl acetic monomer and reclaim low temperature behind the solvent (T≤50 ℃) mutually and be concentrated into muddy the appearance, left standstill crystallization 12 hours, the deionized water recrystallization, get white crystals product 6.4Kg, HPLC content: 98.5%.
Can extract gutta-percha after the slag squeezing.
Claims (1)
1. the method for a preparing chlorogenic acid from eucommia leaves elaboration, it is with the Folium Eucommiae coarse reduction---the deionized water soak at room temperature extracts---squeezing (or centrifugal)---column chromatography enrichment---solvent extraction---coarse crystallization---recrystallization (elaboration);
It is characterized in that:
(1) Folium Eucommiae coarse reduction;
(2) the deionized water soak at room temperature extracts, and temperature 30-40 ℃, regulate pH value to 3.0-3.5, time 30-60 minute/time, repeat 3-4 time,
(3) vat liquor clarification back, adds the reductive agent vacuum and low temperature and concentrates again through the 30-50% ethanol elution with the absorption of macroporous resin upper prop, and wherein macroporous resin is a kind of of AAS, NKA-II, NKA-9, and reductive agent is a kind of of sodium bisulfite, Sulfothiorine,
(4) ethyl acetate extraction elutriant cryoconcentration is to proportion 1.05-1.10, extract with equimultiple water saturation solvent normal temperature, combining extraction liquid, cryoconcentration is to muddy the appearance arranged after reclaiming solvent, leave standstill crystallization, wherein selected extraction solvent is a kind of in propyl carbinol, acetone, the vinyl acetic monomer, also can be its several mixing
(5) recrystallization deionized water 1: 2-1: 4 thermosols, filter stand at low temperature crystallization, cryodrying, finished product.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201010135116A CN101805261A (en) | 2010-03-26 | 2010-03-26 | Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae |
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|---|---|---|---|
| CN201010135116A CN101805261A (en) | 2010-03-26 | 2010-03-26 | Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae |
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| CN101805261A true CN101805261A (en) | 2010-08-18 |
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| CN201010135116A Pending CN101805261A (en) | 2010-03-26 | 2010-03-26 | Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351700A (en) * | 2011-08-15 | 2012-02-15 | 中国科学院过程工程研究所 | Method for separating and purifying chlorogenic acid from eucommia ulmoides leaves |
| CN103012518A (en) * | 2012-12-14 | 2013-04-03 | 湘西自治州奥瑞克医药化工有限责任公司 | Production process for simultaneously extracting asperuloside and chlorogenic acid from folium cortex eucommiae |
| CN103992224A (en) * | 2014-05-05 | 2014-08-20 | 四川九章生物化工科技发展有限公司 | Method for extracting chlorogenic acid from eucommia ulmoides leaves |
| CN105085265A (en) * | 2014-05-09 | 2015-11-25 | 四川九章生物化工科技发展有限公司 | Chlorogenic acid raw material or bulk pharmaceutical chemicals and preparation method and quality detection method therefor |
| US20170050915A1 (en) * | 2014-05-09 | 2017-02-23 | Sichuan Jiuzhang Bilogical Science Adn Technology Co., Ltd. | Crystalline form of chlorogenic acid and preparation method thereof |
| CN109111364A (en) * | 2017-06-22 | 2019-01-01 | 中国烟草总公司广东省公司 | A kind of method of high-pressure pulse electric combination microwave, ultrasonic wave extraction tobacco waste Content of Chlorogenic Acid |
| US10189769B2 (en) | 2014-11-26 | 2019-01-29 | Sichuan Jiuzhang Biological Science And Technology Co., Ltd. | Method for preparation of pharmaceutically acceptable chlorogenic acid |
| CN110240544A (en) * | 2019-06-03 | 2019-09-17 | 西北农林科技大学 | A kind of chlorogenic acid extraction purification method and application |
| CN110483294A (en) * | 2019-09-06 | 2019-11-22 | 湖南理工学院 | One-step method multistage centrifugal fractional extraction separating chlorogenic acid from eucommia ulmoides extracts |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1616402A (en) * | 2003-12-12 | 2005-05-18 | 贵州家诚药业有限责任公司 | Method for extracting and separating chlorogenic acid |
| CN1687435A (en) * | 2005-04-14 | 2005-10-26 | 四川九章生物化工科技发展有限公司 | Technique for producing high purity chlorogenic acid in industrialization scale |
| CN101602668A (en) * | 2009-07-13 | 2009-12-16 | 江西省科学院应用化学研究所 | A method for extracting chlorogenic acid |
-
2010
- 2010-03-26 CN CN201010135116A patent/CN101805261A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1616402A (en) * | 2003-12-12 | 2005-05-18 | 贵州家诚药业有限责任公司 | Method for extracting and separating chlorogenic acid |
| CN1687435A (en) * | 2005-04-14 | 2005-10-26 | 四川九章生物化工科技发展有限公司 | Technique for producing high purity chlorogenic acid in industrialization scale |
| CN101602668A (en) * | 2009-07-13 | 2009-12-16 | 江西省科学院应用化学研究所 | A method for extracting chlorogenic acid |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351700B (en) * | 2011-08-15 | 2013-06-05 | 中国科学院过程工程研究所 | Method for separating and purifying chlorogenic acid from eucommia ulmoides leaves |
| CN102351700A (en) * | 2011-08-15 | 2012-02-15 | 中国科学院过程工程研究所 | Method for separating and purifying chlorogenic acid from eucommia ulmoides leaves |
| CN103012518A (en) * | 2012-12-14 | 2013-04-03 | 湘西自治州奥瑞克医药化工有限责任公司 | Production process for simultaneously extracting asperuloside and chlorogenic acid from folium cortex eucommiae |
| JP2017520616A (en) * | 2014-05-05 | 2017-07-27 | スーチョアン チウチャン バイオロジカル サイエンス アンド テクノロジー カンパニー リミテッド | Extraction method of chlorogenic acid from Tochu leaves |
| CN103992224A (en) * | 2014-05-05 | 2014-08-20 | 四川九章生物化工科技发展有限公司 | Method for extracting chlorogenic acid from eucommia ulmoides leaves |
| CN103992224B (en) * | 2014-05-05 | 2016-08-17 | 四川九章生物化工科技发展有限公司 | A kind of method from extracting chlorogenic acid from Eucommia leaves |
| CN105085265A (en) * | 2014-05-09 | 2015-11-25 | 四川九章生物化工科技发展有限公司 | Chlorogenic acid raw material or bulk pharmaceutical chemicals and preparation method and quality detection method therefor |
| JP2017517476A (en) * | 2014-05-09 | 2017-06-29 | スーチョアン チウチャン バイオロジカル サイエンス アンド テクノロジー カンパニー リミテッド | Chlorogenic acid crystal form and preparation method thereof |
| US20170050915A1 (en) * | 2014-05-09 | 2017-02-23 | Sichuan Jiuzhang Bilogical Science Adn Technology Co., Ltd. | Crystalline form of chlorogenic acid and preparation method thereof |
| CN105085265B (en) * | 2014-05-09 | 2017-11-07 | 四川九章生物科技有限公司 | A kind of chlorogenic acid raw material or bulk drug and preparation method thereof and quality determining method |
| EP3141540A4 (en) * | 2014-05-09 | 2018-01-03 | Sichuan Jiuzhang Biological Science And Technology Co., Ltd | Crystalline form of chlorogenic acid and preparation method therefor |
| US10246401B2 (en) * | 2014-05-09 | 2019-04-02 | Sichuan Jiuzhang Biological Science And Technology Co., Ltd. | Crystalline form of chlorogenic acid and preparation method thereof |
| US10189769B2 (en) | 2014-11-26 | 2019-01-29 | Sichuan Jiuzhang Biological Science And Technology Co., Ltd. | Method for preparation of pharmaceutically acceptable chlorogenic acid |
| CN109111364A (en) * | 2017-06-22 | 2019-01-01 | 中国烟草总公司广东省公司 | A kind of method of high-pressure pulse electric combination microwave, ultrasonic wave extraction tobacco waste Content of Chlorogenic Acid |
| CN109111364B (en) * | 2017-06-22 | 2021-06-22 | 中国烟草总公司广东省公司 | Method for extracting chlorogenic acid from tobacco waste by combining high-voltage pulsed electric field with microwaves and ultrasonic waves |
| CN110240544A (en) * | 2019-06-03 | 2019-09-17 | 西北农林科技大学 | A kind of chlorogenic acid extraction purification method and application |
| CN110483294A (en) * | 2019-09-06 | 2019-11-22 | 湖南理工学院 | One-step method multistage centrifugal fractional extraction separating chlorogenic acid from eucommia ulmoides extracts |
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