CN105175266A - Method for extracting chlorogenic acid and caffeic acid from coffee beans - Google Patents
Method for extracting chlorogenic acid and caffeic acid from coffee beans Download PDFInfo
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Abstract
The invention provides a method for extracting chlorogenic acid and caffeic acid from coffee beans. The whole set of method is put forward for extracting high-purity chlorogenic acid and caffeic acid from coffee beans by conducting degreasing, conducting pyruvic acid water extraction, making the mixture pass through large-hole adsorption resin, conducting concentration, conducting extraction through ethyl acetate, conducting decoloration through activated carbon, and conducting crystallization and recrystallization. The requirement of the whole separation process for environment conditions is not high, the separation time is short, and purity is the highest. Separation materials can be easily obtained and are cheap, the separation operation process is simple and easy to control, crystallization and recrystallization are adopted, the purification efficiency is high, and yield is high.
Description
Art
The present invention relates to one from coffee berry, extract high-purity chlorogenic acid and caffeinic method, belong to the technical field of natural product chemistry.
Background technology
Chlorogenic acid, another name: chlorogenic acid, caffeotannic acid, (1S, 3R, 4R, 5R)-3-[[3-(3,4-dihydroxy phenyl)-1-oxo-2-propenyl] oxygen]-Isosorbide-5-Nitrae, 5-trihydroxy-naphthenic acid; Systematic name: 1,3,4,5-tetrahydroxy hexahydrobenzoic acid-(Caffeic acid ester); Chemical name: CA (3-O-caffeoylquinicacid), plant origin: in the dry flower of caprifoliaceae plant honeysuckle LonicerajaponicaThumb., lonicera hypoglauca miq LonicerahypoglaucaMiq., Lonicera confusa DC. LoniceraconfusaDC. or hair style honeysuckle LoniceradasytylaRehd. or the flower opened at the beginning of being with and Folium Eucommiae.Chlorogenic acid semihydrate is white or micro-yellow needles, 110 DEG C time, become anhydride, with dilute hydrochloric acid thermogenesis coffic acid altogether, and fusing point 208 DEG C, specific rotatory power * α+D=352 ° (C=28).Chlorogenic acid 25 DEG C time in water solubleness be about 4%, be soluble in ethanol, acetone, methyl alcohol polar solvent, be slightly soluble in ethyl acetate, be insoluble in the lipophylic organic solvents such as trichloromethane, ether, benzene.Chlorogenic acid is the ester formed by coffic acid and quinic acid, has ester bond, unsaturated double-bond and polyphenol three l fractions in its molecular structure.From in plant extract process, there is isomerization often through hydrolysis and the migration of intramolecular ester base.Due to the special construction of chlorogenic acid, determine it and ethanol, acetone, methyl alcohol polar solvent can be utilized to extract from plant, but due to the unstable of chlorogenic acid itself, can not high temperature, high light and long-time heating during extraction.It is the most stable when the test liquid of chlorogenic acid is positioned over brown bottle, refrigerator (2 DEG C) is preserved.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.There is more extensive anti-microbial effect, but in vivo can by protein deactivation.Similar to coffic acid, during oral or abdominal injection, the central excitatory of rat can be improved.The small intestinal peristalsis of rat and mouse and the tension force of rat uterus can be increased.There is choleretic effect, the choleresis of rat can be promoted.Have sensitization to people, after sucking the plant dust containing this product, can pant, dermatitis etc., but through the effect of intestinal secretion thing, can to become without allergenic substance after eating.There is hemostasis, increase white cell and antivirus action.Have and shorten blood clotting and the effect in bleeding time.
Chlorogenic acid extensively exists in plant, only in several plant, content is more, as Japanese Honeysuckle, as in sunflower seeds, leaf of Flos Lonicerae, coffee berry, Acer Truncatum Buge leaf, Herba Arctii leaf, Folium Ipomoea, its content is about 1% ~ 8% butt, its content of Different sources is also different, contained chlorogenic acid isomer kind is also different, and also different from the pharmacological action of the chlorogenic acid of different plant.
The moisture content of coffee berry with different processing stages and product, and has very large difference, and the moisture content containing the moist coffee berry of film is about 50 ﹪, and the raw coffee bean of drying is about 10 ﹪ ~ 13 ﹪.Though the content of mineral substance in coffee berry is less, account for 4 ﹪ of raw coffee bean dry matter, very important.It contains multiple different element, and be wherein at most with the content of potassium, accounting for 40 ﹪ of all mineral qualities, is secondly calcium, magnesium, phosphorus, sodium and sulphur etc.Other still has much content at the trace element of PPM level, as zinc, manganese, copper, rubidium etc. more than 33 kinds.Sucrose is topmost free state carbohydrate in raw coffee bean, and its content is different according to kind, source and ripening degree.Polyose is that composition very important in raw coffee bean divides, and accounts for 40% ~ 50 ﹪ of dry amount.In crude protein, raw coffee bean content about 13 ﹪ ~ 16 ﹪, if nitrogenous compound such as deduction caffeine and trigonelline etc., the content of real protein is about 8.8 ﹪ ~ 9.7 ﹪.Also disorderly containing multiple ferment in raw coffee bean, as lipase, proteolytic enzyme, carbohydrate amylase, galactose on hydrolysis ferment and peroxidation ferment etc.The total free aminoacids of raw coffee bean about containing 0.15 ﹪ ~ 0.25 ﹪.Chlorogenic acid has at least the isomer of more than 3 kinds to exist, and its function is mainly coffee plant physiological regulation.The lipid of raw coffee bean is by the coffee oil be present in endosperm and be present in that the outer field wax of coffee berry forms, and the average content of coffee berry is 15 ﹪ of dry amount.Also containing vegeto-alkali, trigonelline, niacin.
The coffee berry working method of publication number a kind of chlorogenic acid-rich that has been the Introduction To Cn Patent of CN1813556A, raw for coffee beans roasting is decocted the coffee berry working method that roasted coffee beans is prepared in process, make high-temperature, high pressure fluid and coffee give birth to beans and contact and implement roasting and decoct process.
Publication number a kind of chlorogenic acid that has been the Introduction To Cn Patent of CN101404891A contains the manufacture method of thing, by the mixture of coffee bean extract (A) and water Combination organic solvent (B) and water (C), after contacting under making the mass ratio of mixed with (A) (B)/(C) reach the condition of 70/30 ~ 99.5/0.5, reclaim solid part.The different chlorogenic acid be reduced of smelling of peculiar smell can be obtained by easy method and contain thing.
The extracting and purifying method of publication number a kind of Chlorogenic Acid of Flos Lonicerae that has been the Introduction To Cn Patent of CN1425643: dry Japanese Honeysuckle is pulverized, Diluted Alcohol is adopted to carry out secondary back extraction to Japanese Honeysuckle, concentrated extract, again with the preliminary edulcoration purification of flocculence, finally adopts Amberlyst process or acid extraction into ethyl acetate method purification refine.
To be the Introduction To Cn Patent of CN1616403 from Japanese Honeysuckle extract the technique preparing chlorogenic acid to publication number: Japanese Honeysuckle adds water or ethanol carries out refluxing extraction, filter, collect filtrate and recycling design, add alcohol settling impurity, spend the night, filter, decompression and solvent recovery, add water appropriate, hold over night, filters, macroporous resin column on filtrate, concentrate with eluent, collect the component containing chlorogenic acid, upper polyamide column, with eluent, collect the component containing chlorogenic acid, concentrated, the refining chlorogenic acid obtaining content and be greater than 95%.
The technique of publication number a kind of chlorogenic acid extracting from Japanese Honeysuckle that has been the Introduction To Cn Patent of CN1199728: the Plus acidic alcohol immersion certain hour of Japanese Honeysuckle, heating and refluxing extraction certain hour, the dregs of a decoction are Plus acidic alcohol reflux certain hour again, merge liquid, decompression recycling ethanol, concentrated, refining.
Current high-quality coffee berry is mainly used in processing coffee, wherein also has most not utilized very well as dead beans etc., and directly use can by coffee with the not mature taste of stock for beans of checkmating.If made full use of by this part coffee berry, coffee plantation income greatly can be improved.Directly adopt coffee berry sour water to carry out chlorogenic acid extracting in addition, owing to containing a large amount of lipid material in coffee berry, chlorogenic acid and coffee acid extraction will be affected.
Summary of the invention
The object of the invention is to overcome the deficiency of prior art and a kind of rational technology is provided, simple to operate, process cycle is short, coffee berry comprehensive utilization degree is high, rapid extraction chlorogenic acid and caffeinic production technique.
The technical solution used in the present invention comprises: carry out degrease process to coffee berry, adopts acid extraction, crosses macroporous adsorbent resin, concentrated, extraction into ethyl acetate, reversed phase column chromatography, decolorizing with activated carbon, ethyl acetate crystallization and height ethyl alcohol recrystallization, obtain chlorogenic acid and coffic acid sterling.
Therefore, the invention provides a kind of from coffee berry chlorogenic acid extracting and caffeinic method, concrete steps comprise:
(1) pulverize dried coffee bean to 10 order ~ 20 order, add ether and carry out cold soaking and carry 3 ~ 4 hours, wherein the weight kg of coffee berry and the volume L of ether is than being 1:4 ~ 10;
(2) ceramic membrane filter once obtains coffee berry residue and containing diethyl ether solution, will carry out concentrating under reduced pressure at 40 ~ 50 DEG C, and reclaim ether, and obtain coffee berry fat containing diethyl ether solution;
(3) coffee berry residue is mixed with acetone soln, room temperature lixiviate, time is 3 ~ 5 hours, wherein the weight kg of coffee berry residue and the volume L of acetone soln are than being 1:5 ~ 10, acetone soln is make after acetone and combined, and acetone volume L and 0.001mol/L aqueous hydrochloric acid volume L is than being 4:1;
(4) ceramic membrane filter once obtains filtrate, and gained filtrate is carried out concentrating under reduced pressure, reclaims acetone, and obtains extracting solution I;
(5) extracting solution I is directly gone up NKA-9 macroporous adsorbent resin, after absorption 30min, with 10% ethanolic soln wash-out of 2BV upper prop liquid, abandon elutriant, use 20% aqueous ethanolic solution wash-out of 3BV upper prop liquid again, collect ethanol eluate I, be concentrated into 1/15 ~ 1/20 of original volume, obtain concentrated solution I, wherein 20% aqueous ethanolic solution refers in 20% ethanolic soln containing 0.00001mol/L hydrochloric acid;
(6) with 45% aqueous ethanolic solution wash-out of 3BV upper prop liquid, collect ethanol eluate II, be concentrated into 1/10 ~ 1/15 of original volume, obtain concentrated solution II, wherein 45% aqueous ethanolic solution refers in 45% ethanolic soln containing 0.01mol/L hydrochloric acid;
(7) with slightly acidic gac, concentrated solution I is decoloured, intermittent stirring decolouring 1h, ceramic membrane filter once obtains filtrate, till this filtrate being concentrated into again the muddy thing of adularescent, be cooled to 1 ~ 4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then obtain coffic acid sterling after recrystallization;
(8) by the ethyl acetate that two to triploid is long-pending, concentrated solution II is extracted, collect the extraction liquid that ethyl acetate is contained on upper strata, concentrating under reduced pressure at 40 ~ 50 DEG C, reclaim ethyl acetate, and obtain chlorogenic acid pure product.
Described filtration procedure is all adopt ceramic membrane filter, and fenestra pore size is 0.22 μm.
Described concentration process is all adopt concentrating under reduced pressure, and temperature controls between 40 ~ 55 DEG C.
In described step (7) to add the weight kg of activated carbon with the volume L ratio of concentrated solution I be 0.1 ~ 5:1.
It is formulated that being formulated as of 10% aqueous ethanolic solution adds the water of 90mL with 10mL dehydrated alcohol; It is formulated that being formulated as of 20% ethanolic soln adds the water of 80mL with 20mL dehydrated alcohol; It is formulated that being formulated as of 45% ethanolic soln adds the water of 55mL with 45mL dehydrated alcohol.
Technique effect
1, skimming treatment can reduce the viscosity of its vat liquor widely, improves filtration velocity, can obtain a large amount of lipid material again, reduce production cost.
2, coffee berry Content of Chlorogenic Acid is high, and the coffee berry chlorogenic acid content of Yunnan Province is up to 14%, and price is low.Use coffee berry substituting as the medicinal material such as Japanese Honeysuckle, Folium Eucommiae, both the utilising efficiency of the residues such as coffee berry had been substantially increased, improve the added value of coffee berry, break away from again the dependence of the medicinal material such as Japanese Honeysuckle, Folium Eucommiae, the complete incidence graph heavy demand of market to the medicinal material such as Japanese Honeysuckle, Folium Eucommiae, extends the medicinal source resource that chlorogenic acid extracts raw material.
3, the inventive method is simple to operate, and raw material sources are convenient, can also obtain lot of coffee lipid material.
4, the reagent that the present invention is used is chemical reagent that is nontoxic, cheap, volume production, and the routine techniques that ripe reagent can be utilized in whole process to reclaim, this greatly reduces to environmental emission waste.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, and following examples are intended to the present invention instead of limitation of the invention further are described.
Embodiment 1
Pulverize dried coffee bean to 10 order ~ 20 order, take 100KG and add 600L ether and carry out cold soaking and carry 3 ~ 4 hours; Ceramic membrane filter once obtains coffee berry residue and containing diethyl ether solution, will carry out concentrating under reduced pressure at 40 ~ 50 DEG C, and reclaim ether, and obtain coffee berry fat 15kg containing diethyl ether solution; The acetone soln (320L acetone is made after mixing with the 0.001mol/L aqueous hydrochloric acid etc. of 80L) getting coffee berry residue 70kg and 400L mixes, room temperature lixiviate, and the time is 3 ~ 5 hours; Ceramic membrane filter once obtains filtrate, and gained filtrate is carried out concentrating under reduced pressure, reclaims acetone, and obtains 60L extracting solution I; Extracting solution I is directly gone up NKA-9 macroporous adsorbent resin, after absorption 30min, with 10% ethanolic soln wash-out of 2BV upper prop liquid, abandon elutriant, use 20% aqueous ethanolic solution (containing the 0.00001mol/L hydrochloric acid) wash-out of 3BV upper prop liquid again, collect ethanol eluate I 150L, be concentrated into 1/15 of original volume, obtain 10L concentrated solution I; With 45% aqueous ethanolic solution (containing the 0.01mol/L hydrochloric acid) wash-out of 3BV upper prop liquid, collect ethanol eluate II 150L, be concentrated into 1/10 of original volume, obtain 15L concentrated solution II; With 2kg slightly acidic gac, concentrated solution I is decoloured, intermittent stirring decolouring 1h, ceramic membrane filter once obtains filtrate, till this filtrate being concentrated into again the muddy thing of adularescent, be cooled to 1 ~ 4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then obtain coffic acid sterling 1.45kg after recrystallization; The ethyl acetate long-pending with two to triploid extracts concentrated solution II, collects the extraction liquid that ethyl acetate is contained on upper strata, concentrating under reduced pressure at 40 ~ 50 DEG C, reclaims ethyl acetate, and obtains chlorogenic acid pure product 12.68kg.Detect through HPLC, the purity of chlorogenic acid sample is 98.5%, and the purity of coffic acid sample is 98.68%.
Embodiment 2
Pulverize dried coffee bean to 10 order ~ 20 order, take 200KG and add 1200L ether and carry out cold soaking and carry 3 ~ 4 hours; Ceramic membrane filter once obtains coffee berry residue and containing diethyl ether solution, will carry out concentrating under reduced pressure at 40 ~ 50 DEG C, and reclaim ether, and obtain coffee berry fat 35kg containing diethyl ether solution; The acetone soln (480L acetone is made after mixing with the 0.001mol/L aqueous hydrochloric acid etc. of 120L) getting coffee berry residue 100kg and 600L mixes, room temperature lixiviate, and the time is 3 ~ 5 hours; Ceramic membrane filter once obtains filtrate, and gained filtrate is carried out concentrating under reduced pressure, reclaims acetone, and obtains 100L extracting solution I; Extracting solution I is directly gone up NKA-9 macroporous adsorbent resin, after absorption 30min, with 10% ethanolic soln wash-out of 2BV upper prop liquid, abandon elutriant, use 20% aqueous ethanolic solution (containing the 0.00001mol/L hydrochloric acid) wash-out of 3BV upper prop liquid again, collect 200L ethanol eluate I, be concentrated into 1/20 of original volume, obtain 10L concentrated solution I; With 45% aqueous ethanolic solution (containing the 0.01mol/L hydrochloric acid) wash-out of 3BV upper prop liquid, collect 200L ethanol eluate II, be concentrated into 1/10 of original volume, obtain 20L concentrated solution II; With 4kg slightly acidic gac, concentrated solution I is decoloured, intermittent stirring decolouring 1h, ceramic membrane filter once obtains filtrate, till this filtrate being concentrated into again the muddy thing of adularescent, be cooled to 1 ~ 4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then obtain coffic acid sterling 2.87kg after recrystallization; The ethyl acetate long-pending with two to triploid extracts concentrated solution II, collects the extraction liquid that ethyl acetate is contained on upper strata, concentrating under reduced pressure at 40 ~ 50 DEG C, reclaims ethyl acetate, and obtains chlorogenic acid pure product 18.54kg.Detect through HPLC, the purity of chlorogenic acid sample is 98.67%, and the purity of coffic acid sample is 98.89%.
Embodiment 3
Pulverize dried coffee bean to 10 order ~ 20 order, take 400KG and add 2000L ether and carry out cold soaking and carry 3 ~ 4 hours; Ceramic membrane filter once obtains coffee berry residue and containing diethyl ether solution, will carry out concentrating under reduced pressure at 40 ~ 50 DEG C, and reclaim ether, and obtain coffee berry fat 70kg containing diethyl ether solution; The acetone soln (960L acetone is made after mixing with the 0.001mol/L aqueous hydrochloric acid etc. of 240L) getting coffee berry residue 200kg and 1200L mixes, room temperature lixiviate, and the time is 3 ~ 5 hours; Ceramic membrane filter once obtains filtrate, and gained filtrate is carried out concentrating under reduced pressure, reclaims acetone, and obtains 200L extracting solution I; Extracting solution I is directly gone up NKA-9 macroporous adsorbent resin, after absorption 30min, with 10% ethanolic soln wash-out of 2BV upper prop liquid, abandon elutriant, use 20% aqueous ethanolic solution (containing the 0.00001mol/L hydrochloric acid) wash-out of 3BV upper prop liquid again, collect ethanol eluate I 400L, be concentrated into 1/20 of original volume, obtain 20L concentrated solution I; With 45% aqueous ethanolic solution (containing the 0.01mol/L hydrochloric acid) wash-out of 3BV upper prop liquid, collect ethanol eluate II 400L, be concentrated into 1/16 of original volume, obtain 25L concentrated solution II; With 5kg slightly acidic gac, concentrated solution I is decoloured, intermittent stirring decolouring 1h, ceramic membrane filter once obtains filtrate, till this filtrate being concentrated into again the muddy thing of adularescent, be cooled to 1 ~ 4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then obtain coffic acid sterling 5.87kg after recrystallization; The ethyl acetate long-pending with two to triploid extracts concentrated solution II, collects the extraction liquid that ethyl acetate is contained on upper strata, concentrating under reduced pressure at 40 ~ 50 DEG C, reclaims ethyl acetate, and obtains chlorogenic acid pure product 36.35kg.Detect through HPLC, the purity of chlorogenic acid sample is 98.77%, and the purity of coffic acid sample is 99.15%.
Claims (4)
1., from coffee berry chlorogenic acid extracting and a caffeinic method, concrete steps comprise:
(1) pulverize dried coffee bean to 10 order ~ 20 order, add ether and carry out cold soaking and carry 3 ~ 4 hours, wherein the weight kg of coffee berry and the volume L of ether is than being 1:4 ~ 10;
(2) ceramic membrane filter once obtains coffee berry residue and containing diethyl ether solution, will carry out concentrating under reduced pressure at 40 ~ 50 DEG C, and reclaim ether, and obtain coffee berry fat containing diethyl ether solution;
(3) coffee berry residue is mixed with acetone soln, room temperature lixiviate, time is 3 ~ 5 hours, wherein the weight kg of coffee berry residue and the volume L of acetone soln are than being 1:5 ~ 10, acetone soln is make after acetone and combined, and acetone volume L and 0.001mol/L aqueous hydrochloric acid volume L is than being 4:1;
(4) ceramic membrane filter once obtains filtrate, and gained filtrate is carried out concentrating under reduced pressure, reclaims acetone, and obtains extracting solution I;
(5) extracting solution I is directly gone up NKA-9 macroporous adsorbent resin, after absorption 30min, with 10% ethanolic soln wash-out of 2BV upper prop liquid, abandon elutriant, use 20% aqueous ethanolic solution wash-out of 3BV upper prop liquid again, collect ethanol eluate I, be concentrated into 1/15 ~ 1/20 of original volume, obtain concentrated solution I, wherein 20% aqueous ethanolic solution refers in 20% ethanolic soln containing 0.00001mol/L hydrochloric acid;
(6) with 45% aqueous ethanolic solution wash-out of 3BV upper prop liquid, collect ethanol eluate II, be concentrated into 1/10 ~ 1/15 of original volume, obtain concentrated solution II, wherein 45% aqueous ethanolic solution refers in 45% ethanolic soln containing 0.01mol/L hydrochloric acid;
(7) with slightly acidic gac, concentrated solution I is decoloured, intermittent stirring decolouring 1h, ceramic membrane filter once obtains filtrate, till this filtrate being concentrated into again the muddy thing of adularescent, be cooled to 1 ~ 4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then obtain coffic acid sterling after recrystallization;
(8) by the ethyl acetate that two to triploid is long-pending, concentrated solution II is extracted, collect the extraction liquid that ethyl acetate is contained on upper strata, concentrating under reduced pressure at 40 ~ 50 DEG C, reclaim ethyl acetate, and obtain chlorogenic acid pure product.
2. method according to claim 1, wherein filtration procedure is all adopt ceramic membrane filter, and fenestra pore size is 0.22 μm.
3. method according to claim 1, wherein concentration process is all adopt concentrating under reduced pressure, and temperature controls between 40 ~ 55 DEG C.
4. method according to claim 1, wherein in step (7) to add the weight kg of activated carbon with the volume L ratio of concentrated solution I be 0.1 ~ 5:1.
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| CN108586242A (en) * | 2018-04-02 | 2018-09-28 | 太阳树（厦门）生物工程有限公司 | A method of extracting low-caffeine chlorogenic acid from green coffee bean |
| CN110305007A (en) * | 2019-07-25 | 2019-10-08 | 广西民族大学 | One kind extracting caffeinic method from a silk fabric |
| CN110746303A (en) * | 2019-11-15 | 2020-02-04 | 云南大学 | Coffee bean processing method and extract purification method thereof |
| CN111676264A (en) * | 2020-06-28 | 2020-09-18 | 湖南杰萃生物技术有限公司 | Method for extracting caffeic acid from rosemary |
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| CN113336755A (en) * | 2021-06-04 | 2021-09-03 | 北京理工大学 | Method for separating and purifying trigonelline, chlorogenic acid and caffeine |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107141218A (en) * | 2017-07-17 | 2017-09-08 | 湖南楚宏生物科技有限公司 | A kind of method that chlorogenic acid and gallic acid are produced from coffee bean |
| CN107235840A (en) * | 2017-07-17 | 2017-10-10 | 长沙爱扬医药科技有限公司 | A kind of method of the chlorogenic acid extracting from coffee bean and tannin |
| CN108586242A (en) * | 2018-04-02 | 2018-09-28 | 太阳树（厦门）生物工程有限公司 | A method of extracting low-caffeine chlorogenic acid from green coffee bean |
| CN110305007A (en) * | 2019-07-25 | 2019-10-08 | 广西民族大学 | One kind extracting caffeinic method from a silk fabric |
| CN110746303A (en) * | 2019-11-15 | 2020-02-04 | 云南大学 | Coffee bean processing method and extract purification method thereof |
| CN111676264A (en) * | 2020-06-28 | 2020-09-18 | 湖南杰萃生物技术有限公司 | Method for extracting caffeic acid from rosemary |
| CN111676264B (en) * | 2020-06-28 | 2023-05-16 | 湖南杰萃生物技术有限公司 | Method for extracting caffeic acid from rosemary |
| CN111991847A (en) * | 2020-09-03 | 2020-11-27 | 河北瑞龙生物科技有限公司 | Preparation method of coffee bean hull extract |
| CN111991847B (en) * | 2020-09-03 | 2022-03-04 | 河北瑞龙生物科技有限公司 | Coffee bean hull extract and preparation method and application thereof |
| CN113173848A (en) * | 2021-05-12 | 2021-07-27 | 南京合谷生命生物科技有限公司 | Method for extracting and separating caffeic acid from fermentation liquor |
| CN113173848B (en) * | 2021-05-12 | 2022-02-18 | 南京合谷生命生物科技有限公司 | Method for extracting and separating caffeic acid from fermentation liquor |
| CN113336755A (en) * | 2021-06-04 | 2021-09-03 | 北京理工大学 | Method for separating and purifying trigonelline, chlorogenic acid and caffeine |
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