CN103664611B - Method for extracting chlorogenic acid from Robusta coffee seeds - Google Patents
Method for extracting chlorogenic acid from Robusta coffee seeds Download PDFInfo
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- CN103664611B CN103664611B CN201310630722.0A CN201310630722A CN103664611B CN 103664611 B CN103664611 B CN 103664611B CN 201310630722 A CN201310630722 A CN 201310630722A CN 103664611 B CN103664611 B CN 103664611B
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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 24
- 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 24
- 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 24
- 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 24
- 229940074393 chlorogenic acid Drugs 0.000 title claims abstract description 24
- 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 24
- 235000001368 chlorogenic acid Nutrition 0.000 title claims abstract description 24
- 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 24
- 238000000034 method Methods 0.000 title claims abstract description 18
- 235000002187 Coffea robusta Nutrition 0.000 title abstract 3
- 239000012528 membrane Substances 0.000 claims abstract description 28
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 24
- 239000000843 powder Substances 0.000 claims abstract description 16
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 238000001471 micro-filtration Methods 0.000 claims abstract description 14
- 238000001728 nano-filtration Methods 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910001868 water Inorganic materials 0.000 claims abstract description 12
- 238000000605 extraction Methods 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 7
- 238000001704 evaporation Methods 0.000 claims abstract description 7
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims abstract description 7
- 229910052939 potassium sulfate Inorganic materials 0.000 claims abstract description 7
- 235000011151 potassium sulphates Nutrition 0.000 claims abstract description 7
- 239000001509 sodium citrate Substances 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 230000008020 evaporation Effects 0.000 claims abstract description 6
- 239000012466 permeate Substances 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 235000013399 edible fruits Nutrition 0.000 claims description 11
- 238000001556 precipitation Methods 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 10
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims description 6
- 229940038773 trisodium citrate Drugs 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000011148 porous material Substances 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 3
- 238000000227 grinding Methods 0.000 abstract description 2
- 239000003208 petroleum Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 abstract 4
- 239000002244 precipitate Substances 0.000 abstract 3
- 239000013078 crystal Substances 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 2
- 238000002386 leaching Methods 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000001120 potassium sulphate Substances 0.000 abstract 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 102100036264 Glucose-6-phosphatase catalytic subunit 1 Human genes 0.000 description 1
- 101710099339 Glucose-6-phosphatase catalytic subunit 1 Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000003591 anti-choleraic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002790 anti-mutagenic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000002279 cholagogic effect Effects 0.000 description 1
- 239000000731 choleretic agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for extracting chlorogenic acid, in particular to a method for extracting the chlorogenic acid from Robusta coffee seeds, and belongs to the technical field of extraction of natural plants. The method comprises the following steps: getting Robusta coffee seeds, drying in sunlight, and grinding into powder; adding water, potassium sulphate and sodium citrate, heating for extraction to obtain a leaching solution; filtering the leaching solution by using a microfiltration membrane to obtain microfiltration permeating liquid; performing ultrafiltration on the microfiltration permeating liquid to obtain ultrafiltration permeating liquid; concentrating the ultrafiltration permeating liquid by using a nanofiltration membrane to obtain a concentrated solution; further evaporating the concentrated solution, then adding an aqueous solution of ethanol to generate precipitate, and after standing, taking out the precipitate at the lower part; adding water into the precipitate, adjusting pH, uniformly mixing, then adding petroleum ether, extracting, and collecting an organic phase; concentrating the organic phase through evaporation, crystallizing through cooling, filtering out crystals, and drying the crystals to obtain the chlorogenic acid. By adopting the method, a new way for obtaining the chlorogenic acid is found; the method is simple in operation process, high in product yield and good in product purity.
Description
Technical field
The present invention relates to a kind of extracting method of chlorogenic acid, particularly relate to the method for chlorogenic acid extracting in a kind of seed of therefrom fruit coffee, belong to extracted form natural plant technical field.
Background technology
Chlorogenic acid is considered to the principle active component of numerous medicinal material and Chinese patent medicine antibacterial and detoxicating, anti-inflammatory and choleretic, usually by as qualitative even quantitative index.It is reported, the primary bioactivity of chlorogenic acid has (1) to the restraining effect of Unidasa and G-6-Pase; (2) to removing and the lipoid peroxidization resistant of free radical; (3) anti-mutagenic activity; (4) hepatic cholagogic effect; (5) effect such as antibacterial, antiviral and spasmolysis.
Chlorogenic acid or a kind of new and effective phenolic natural antioxidants, can replace or partly replace the antioxidant of synthetic conventional at present in some food.As added a small amount of chlorogenic acid in lard, the antioxidative stabilizer of lard can be improved, increasing the quality guaranteed period.Chlorogenic acid has flavouring and color-protecting function, can be used for the fresh-keeping of food and fruit.Chlorogenic acid or a kind of good foodstuff additive, can be made into the Foods or drinks with nourishing function.
The extracting method of chlorogenic acid includes: the extraction of reflux extraction, ultrasonic extraction, microwave loss mechanisms, percolation, decocting method extraction, restricted-access media etc., but these methods all have complicated operation, equipment is uncommon, and yield is low, the shortcoming and defect that purity is low.
Summary of the invention
The object of the invention is: provide a kind of can the method for chlorogenic acid extracting in the seed of therefrom fruit coffee, the technical scheme of employing is as follows:
The method of chlorogenic acid extracting in the seed of therefrom fruit coffee, comprises the steps:
1st step, by weight, get 30 ~ 40 parts, the seed of middle fruit coffee, after drying, grind into powder, then the water, potassium sulfate 1 ~ 3 part, the Trisodium Citrate 1 ~ 3 part that add 10 ~ 15 times of weight, be warming up to 80 ~ 90 DEG C of lixiviates, time is 2 ~ 4 hours, obtains vat liquor;
2nd step, vat liquor to be filtered by microfiltration membrane, obtain MF permeate liquid;
3rd step, MF permeate liquid is carried out ultrafiltration, obtain ultrafiltration permeate;
4th step, ultrafiltration permeate nanofiltration membrane to be concentrated, obtain concentrated solution;
5th step, concentrated solution is evaporated to volume-diminished is further 40% ~ 50%, then adds the aqueous ethanolic solution that mass concentration is more than 98%, generation is precipitated, and after leaving standstill, takes off the precipitation in portion;
6th step, in precipitation, add the water of 40 ~ 50 parts, regulate pH to 9.0 ~ 10.0, mix, then add the sherwood oil of 30 ~ 40 parts, extraction, collect organic phase;
7th step, by organic phase evaporation concentration, until volume-diminished is 15% ~ 25%, then crystallisation by cooling, after crystallization being leached, dries.
Preferably, in the 1st step, powder pulverized powder order number is 200 ~ 400 orders;
Preferably, in the 2nd step, the mean pore size of microfiltration membrane is 100 ~ 500 nm;
Preferably, in the 3rd step, the molecular weight cut-off of ultra-filtration membrane is 500000 ~ 1000000Da;
Preferably, in the 4th step, the molecular weight cut-off of nanofiltration membrane is 300 ~ 800Da;
Preferably, in the 6th step, functional quality concentration be 1% ~ 3% sodium hydroxide solution pH is regulated;
Preferably, in the 7th step, the temperature of oven dry is 110 DEG C ~ 120 DEG C, and the time of oven dry is 4 ~ 6 hours.
In method provided by the invention, in 1st step, grinding and the object that adds potassium sulfate and Trisodium Citrate are that active substance is separated out better, in 2nd step, some large granule foreigns are removed in the effect of microfiltration membrane, in 3rd step, some colloidal impurity, albumen etc. are removed in the effect of ultrafiltration, the effect of the nanofiltration of the 4th step is that active substance is concentrated, and simultaneously some inorganic salt through, the object of the 5th step uses ethanol by active precipitation, then obtain chlorogenic acid by the mode of petroleum ether extraction.
beneficial effect
The present invention obtains chlorogenic acid to have found a new approach, and the operation sequence of the method is simple, and product yield is high, and purity is good.
Embodiment
Embodiment 1
1st step, get the seed 30Kg of middle fruit coffee, after drying, grind into powder, then the water, potassium sulfate 1Kg, the Trisodium Citrate 1Kg that add 10 times of weight, be warming up to 80 DEG C of lixiviates, the time is 2 hours, obtains vat liquor;
2nd step, vat liquor to be filtered by microfiltration membrane, obtain MF permeate liquid;
3rd step, MF permeate liquid is carried out ultrafiltration, obtain ultrafiltration permeate;
4th step, ultrafiltration permeate nanofiltration membrane to be concentrated, obtain concentrated solution;
5th step, concentrated solution is evaporated to volume-diminished is further 40%, then adds the aqueous ethanolic solution that mass concentration is more than 98%, generation is precipitated, and after leaving standstill, takes off the precipitation in portion;
6th step, in precipitation, add the water of 40Kg, regulate pH to 9.0, mix, then add the sherwood oil of 30Kg, extraction, collect organic phase;
7th step, by organic phase evaporation concentration, until volume-diminished is 15%, then crystallisation by cooling, after crystallization being leached, dries.
In 1st step, powder pulverized powder order number is 200 ~ 400 orders; In 2nd step, the mean pore size of microfiltration membrane is 100 nm; In 3rd step, the molecular weight cut-off of ultra-filtration membrane is 500000Da; In 4th step, the molecular weight cut-off of nanofiltration membrane is 300Da; In 6th step, functional quality concentration be 1% sodium hydroxide solution pH is regulated; In 7th step, the temperature of oven dry is 110 DEG C, and the time of oven dry is 4 hours.
Obtain chlorogenic acid 31 g altogether, purity 64.1%.
Embodiment 2
1st step, get the seed 40Kg of middle fruit coffee, after drying, grind into powder, then the water, potassium sulfate 3Kg, the Trisodium Citrate 3Kg that add 15 times of weight, be warming up to 90 DEG C of lixiviates, the time is 4 hours, obtains vat liquor;
2nd step, vat liquor to be filtered by microfiltration membrane, obtain MF permeate liquid;
3rd step, MF permeate liquid is carried out ultrafiltration, obtain ultrafiltration permeate;
4th step, ultrafiltration permeate nanofiltration membrane to be concentrated, obtain concentrated solution;
5th step, concentrated solution is evaporated to volume-diminished is further 50%, then adds the aqueous ethanolic solution that mass concentration is more than 98%, generation is precipitated, and after leaving standstill, takes off the precipitation in portion;
6th step, in precipitation, add the water of 50Kg, regulate pH to 10.0, mix, then add the sherwood oil of 40Kg, extraction, collect organic phase;
7th step, by organic phase evaporation concentration, until volume-diminished is 25%, then crystallisation by cooling, after crystallization being leached, dries.
In 1st step, powder pulverized powder order number is 200 ~ 400 orders; In 2nd step, the mean pore size of microfiltration membrane is 500 nm; In 3rd step, the molecular weight cut-off of ultra-filtration membrane is 1000000Da; In 4th step, the molecular weight cut-off of nanofiltration membrane is 800Da; In 6th step, functional quality concentration be 3% sodium hydroxide solution pH is regulated; In 7th step, the temperature of oven dry is 120 DEG C, and the time of oven dry is 6 hours.
Obtain chlorogenic acid 32 g altogether, purity 64.8%.
Embodiment 3
1st step, get the seed 50Kg of middle fruit coffee, after drying, grind into powder, then the water, potassium sulfate 2Kg, the Trisodium Citrate 2Kg that add 12 times of weight, be warming up to 84 DEG C of lixiviates, the time is 3 hours, obtains vat liquor;
2nd step, vat liquor to be filtered by microfiltration membrane, obtain MF permeate liquid;
3rd step, MF permeate liquid is carried out ultrafiltration, obtain ultrafiltration permeate;
4th step, ultrafiltration permeate nanofiltration membrane to be concentrated, obtain concentrated solution;
5th step, concentrated solution is evaporated to volume-diminished is further 45%, then adds the aqueous ethanolic solution that mass concentration is more than 98%, generation is precipitated, and after leaving standstill, takes off the precipitation in portion;
6th step, in precipitation, add the water of 45Kg, regulate pH to 9.5, mix, then add the sherwood oil of 35Kg, extraction, collect organic phase;
7th step, by organic phase evaporation concentration, until volume-diminished is 20%, then crystallisation by cooling, after crystallization being leached, dries.
In 1st step, powder pulverized powder order number is 200 ~ 400 orders; In 2nd step, the mean pore size of microfiltration membrane is 200 nm; In 3rd step, the molecular weight cut-off of ultra-filtration membrane is 800000; In 4th step, the molecular weight cut-off of nanofiltration membrane is 500Da; In 6th step, functional quality concentration be 2% sodium hydroxide solution pH is regulated; In 7th step, the temperature of oven dry is 115 DEG C, and the time of oven dry is 5 hours.
Obtain chlorogenic acid 37 g altogether, purity 67.8%.
Claims (1)
1. the method for chlorogenic acid extracting in the seed of a therefrom fruit coffee, it is characterized in that, comprise the steps: the 1st step, get the seed 50Kg of middle fruit coffee, after drying, grind into powder, then the water, potassium sulfate 2Kg, the Trisodium Citrate 2Kg that add 12 times of weight, be warming up to 84 DEG C of lixiviates, time is 3 hours, obtains vat liquor; 2nd step, vat liquor to be filtered by microfiltration membrane, obtain MF permeate liquid; 3rd step, MF permeate liquid is carried out ultrafiltration, obtain ultrafiltration permeate; 4th step, ultrafiltration permeate nanofiltration membrane to be concentrated, obtain concentrated solution; 5th step, concentrated solution is evaporated to volume-diminished is further 45%, then adds the aqueous ethanolic solution that mass concentration is more than 98%, generation is precipitated, and after leaving standstill, takes off the precipitation in portion; 6th step, in precipitation, add the water of 45Kg, regulate pH to 9.5, mix, then add the sherwood oil of 35Kg, extraction, collect organic phase; 7th step, by organic phase evaporation concentration, until volume-diminished is 20%, then crystallisation by cooling, after crystallization being leached, dries; In 1st step, powder pulverized powder order number is 200 ~ 400 orders; In 2nd step, the mean pore size of microfiltration membrane is 200 nm; In 3rd step, the molecular weight cut-off of ultra-filtration membrane is 800000; In 4th step, the molecular weight cut-off of nanofiltration membrane is 500Da; In 6th step, functional quality concentration be 2% sodium hydroxide solution pH is regulated; In 7th step, the temperature of oven dry is 115 DEG C, and the time of oven dry is 5 hours; Obtain chlorogenic acid 37 g altogether, purity 67.8%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310630722.0A CN103664611B (en) | 2013-12-02 | 2013-12-02 | Method for extracting chlorogenic acid from Robusta coffee seeds |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310630722.0A CN103664611B (en) | 2013-12-02 | 2013-12-02 | Method for extracting chlorogenic acid from Robusta coffee seeds |
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| CN103664611A CN103664611A (en) | 2014-03-26 |
| CN103664611B true CN103664611B (en) | 2015-05-20 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109096110A (en) * | 2018-09-05 | 2018-12-28 | 安徽龙津生物科技有限公司 | A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean |
| CN111574372B (en) * | 2020-06-05 | 2023-03-28 | 精晶药业股份有限公司 | Method for extracting chlorogenic acid from Chinese herbal medicine by electrodialysis method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101704748A (en) * | 2009-09-28 | 2010-05-12 | 南京泽朗医药科技有限公司 | Method for extracting chlorogenic acid |
| CN102040519A (en) * | 2009-10-22 | 2011-05-04 | 湖北老龙洞杜仲开发有限公司 | Method for preparing chlorogenic acid in Eucommia ulmoides leaves |
| CN103232346A (en) * | 2013-04-06 | 2013-08-07 | 西安宏冠生物科技有限公司 | Production process for extraction of chlorogenic acid from green coffee bean |
| CN103360258A (en) * | 2013-08-08 | 2013-10-23 | 内蒙古鑫吉利生物科技有限公司 | Method for extracting chlorogenic acid from coffee beans |
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2013
- 2013-12-02 CN CN201310630722.0A patent/CN103664611B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101704748A (en) * | 2009-09-28 | 2010-05-12 | 南京泽朗医药科技有限公司 | Method for extracting chlorogenic acid |
| CN102040519A (en) * | 2009-10-22 | 2011-05-04 | 湖北老龙洞杜仲开发有限公司 | Method for preparing chlorogenic acid in Eucommia ulmoides leaves |
| CN103232346A (en) * | 2013-04-06 | 2013-08-07 | 西安宏冠生物科技有限公司 | Production process for extraction of chlorogenic acid from green coffee bean |
| CN103360258A (en) * | 2013-08-08 | 2013-10-23 | 内蒙古鑫吉利生物科技有限公司 | Method for extracting chlorogenic acid from coffee beans |
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Effective date of registration: 20201123 Address after: 030000 Room 351, 3502 and 503, Building 4, Hatching Base No. 11 Kangshou Street, Tanghuai Park, Taiyuan City, Shanxi Comprehensive Reform Demonstration Zone Patentee after: Shanxi Na'an Biotechnology Co.,Ltd. Address before: 226000 Dalian Road East, Tongzhou Development Zone, Nantong, Jiangsu, Tongzhou District Patentee before: NANTONG RONGTAI BIO-TECHNOLOGY Co.,Ltd. |
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