CN105175266B - One kind chlorogenic acid extracting and caffeinic method from coffee bean - Google Patents
One kind chlorogenic acid extracting and caffeinic method from coffee bean Download PDFInfo
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- CN105175266B CN105175266B CN201510724941.4A CN201510724941A CN105175266B CN 105175266 B CN105175266 B CN 105175266B CN 201510724941 A CN201510724941 A CN 201510724941A CN 105175266 B CN105175266 B CN 105175266B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
Abstract
High-purity chlorogenic acid and caffeinic method are extracted from coffee bean the invention provides one kind, propose extraction high-purity chlorogenic acid and caffeic acid in a whole set of coffee bean, extracted using pyruvic acid water after first degreasing, cross macroporous absorbent resin, concentration, ethyl acetate extraction, decolorizing with activated carbon, crystallization recrystallization, obtains chlorogenic acid and caffeic acid sterling.Less demanding to environmental condition in whole separation process, disengaging time is shorter, purity highest.Separation material is easy to get cheaply, and separation operation process is simple, easy to control, is recrystallized using crystallization, and purification efficiency is high, and high income.
Description
Art
High-purity chlorogenic acid and caffeinic method are extracted from coffee bean the present invention relates to one kind, belongs to natural products
Technical field.
Background technology
Chlorogenic acid, alias：Chlorogenic acid, caffeotannic acid, (1S, 3R, 4R, 5R) -3- [[3- (3,4- dihydroxy phenyl) -1- oxygen
Generation -2- acrylic] oxygen]-Isosorbide-5-Nitrae, 5- trihydroxy naphthenic acids；System name：1,3,4,5- tetrahydroxy cyclohexane-carboxylic acid-(3,4-
Dihydroxycinnamic acid ester)；Chemical name：CA (3-O-caffeoyl quinic acid), plant origin：For
Caprifoliaceae plant honeysuckle Lonicera japonica Thumb., lonicera hypoglauca miq Lonicera hypoglauca Miq., mountain silver
What the dry flower or band of flower Lonicera confusa DC. or hair style honeysuckle Lonicera dasytyla Rehd. were just opened
In flower and folium cortex eucommiae.Chlorogenic acid semihydrate is white or slightly yellow acicular crystal, is changed into anhydride at 110 DEG C, with dilute salt
Heat produces caffeic acid, 208 DEG C of fusing point ,+D=352 ° of specific rotatory power * α (C=28) altogether for acid.Chlorogenic acid solubility in water at 25 DEG C
About 4%, ethanol, acetone, methyl alcohol polar solvent are soluble in, ethyl acetate is slightly soluble in, it is insoluble in chloroform, ether, benzene
Deng lipophylic organic solvents.Chlorogenic acid is the ester formed by caffeic acid and chinic acid, has ester bond, unsaturation double in its molecular structure
Three l fractions of key and polyhydric phenols.From during plant extract, migrated often through hydrolysis and intramolecular ester group and sent out
Raw isomerization.Due to the special construction of chlorogenic acid, determine that it can utilize ethanol, acetone, methyl alcohol polar solvent from plant
In extract, but the unstability due to chlorogenic acid in itself, high temperature, high light and long-time heating are unable to during extraction.Green original
The test liquid of acid is positioned over when brown bottle, (2 DEG C) of refrigerator are preserved to be stablized the most.Chlorogenic acid is considered as numerous medicinal materials and Chinese patent drug
The principle active component of antibacterial and detoxicating, anti-inflammatory and choleretic, is normally used as qualitative or even quantitative index.It is reported that chlorogenic acid
Primary bioactivity has (1) to hyaluronidase and the inhibitory action of G-6-Pase；(2) removing to free radical and
Lipoid peroxidization resistant；(3) antimutagenesis；(4) hepatic cholagogic effect；(5) effect such as antibacterial, antiviral and spasmolysis.Tool
There is wide antibacterial action, but can be inactivated by protein in vivo.It is similar to caffeic acid, during oral or intraperitoneal injection, can improve
The central excitatory of rat.The small bowel peristalsis and the tension force of rat uterus of rat and mouse can be increased.There is choleretic effect, can promote
The choleresis of rat.There is sensitization to people, after plant dust of the suction containing this product, asthma, dermatitis etc., but food can occur
Can be acted on through intestinal secretion thing after entering, be changed into without allergenic substance.There is hemostasis, increase white blood cell and antivirus action.With contracting
Short blood clotting and the effect in bleeding time.
Chlorogenic acid is widely present in plant, and only content is more in several plant, such as honeysuckle, such as sunflower seeds, gold and silver
In floral leaf, coffee bean, Acer truncatum leaves, burdock leaf, sweet potato leaves, its content in 1%~8% butt or so, different sources its contents
Also different, contained chlorogenic acid isomers species is also different, and the chlorogenic acid from different plants pharmacological action not yet
Equally.
The moisture of coffee bean has very big difference with different processing stages and product, the moist coffee bean containing film
Moisture be about 50 ﹪, and the fresh coffee beans of drying are about 10 ﹪~13 ﹪.Though content of the mineral matter in coffee bean compared with
It is few, 4 ﹪ of fresh coffee beans dry matter are accounted for, but it is critically important.It contains various different elements, wherein with the content of potassium as most
It is many, 40 ﹪ of all mineral qualities are accounted for, secondly it is calcium, magnesium, phosphorus, sodium and sulphur etc..Other still have many contents in PPM levels
Trace element, such as zinc, manganese, copper, more than 33 kinds of rubidium.Sucrose is topmost free state carbohydrate in fresh coffee beans, its content according to
Kind, source and maturity and it is different.Polysaccharide is critically important group composition in fresh coffee beans, account for dry amount 40%~
50 ﹪.In terms of crude protein, ﹪~16 ﹪ of fresh coffee beans content about 13, if deducting the nitrogen-containing compounds such as caffeine and trigonelline,
The content of real protein is about 8.8 ﹪~9.7 ﹪.It is also disorderly containing various ferment in fresh coffee beans, such as lipase, albumen
Matter amylase, carbohydrate amylase, galactose on hydrolysis ferment and peroxidating ferment etc..Fresh coffee beans about containing 0.15 ﹪~
The free amino acid of 0.25 ﹪.The isomeric compound that at least more than 3 kinds of chlorogenic acid is present, and its function essentially consists in coffee plant physiology
Regulation.The lipid of fresh coffee beans is made up of the caffeol being present in endosperm and the wax for being present in coffee bean outer layer, coffee
The average content of coffee beans is 15 ﹪ of dry amount.Also contain vegetable soda, trigonelline, niacin.
A kind of coffee bean processing of chlorogenic acid-rich of the Introduction To Cn Patent of Publication No. CN1813556A
Method, the coffee bean processing method that treatment prepares roasted coffee beans is decocted by green coffee roasting, high-temperature, high pressure fluid is given birth to coffee
Beans contact implements roasting and decocts treatment.
A kind of chlorogenic acid of the Introduction To Cn Patent of Publication No. CN101404891A contains the manufacture method of thing, by coffee
Coffee beans extract (A) and water Combination organic solvent (B) and the mixture of water (C), make (B)/(C's) mixed with (A)
Mass ratio is reached after be in contact under conditions of 70/30~99.5/0.5, reclaims solid part.Can be obtained by easy method
The different chlorogenic acid being reduced of smelling of peculiar smell contains thing.
A kind of method for extraction and purification of Chlorogenic Acid of Flos Lonicerae of the Introduction To Cn Patent of Publication No. CN1425643：It is dry
Honeysuckle is crushed, and secondary back extraction is carried out to honeysuckle using Diluted Alcohol, and concentrated extract is pure with the preliminary removal of impurities of flocculence again
Change, it is finally refined using Amberlyst process or acid ethyl acetate extraction purifying.
The Introduction To Cn Patent of Publication No. CN1616403 extraction prepares chlorogenic acid from honeysuckle technique：Gold and silver
Flower adds water or ethanol carries out refluxing extraction, filtering, collects filtrate and recycling design, plus ethanol precipitation impurity, and overnight, filtering subtracts
Pressure recycling design, adds water appropriate, stands overnight, and filters, macroporous resin column on filtrate, is concentrated with eluant, eluent, collects and contains green original
The component of acid, upper polyamide column, with eluent, collects the component containing chlorogenic acid, and concentration is refining to obtain content and is more than
95% chlorogenic acid.
A kind of technique of the chlorogenic acid extracting from honeysuckle of the Introduction To Cn Patent of Publication No. CN1199728：Gold and silver
Spend Plus acidic ethanol immersion certain hour, heating and refluxing extraction certain hour, the dregs of a decoction Plus acidic timing of alcohol reflux extraction one again
Between, merge liquid, ethanol is recovered under reduced pressure, concentrate, refine.
Current high-quality coffee bean is mainly used in processing coffee, wherein there is most such as dead beans not obtain very
Coffee is directly carried stock sentimental taste by dead beans by good utilisation using meeting.If this part coffee bean is made full use of, can significantly
Improve coffee plantation income.Chlorogenic acid extracting is directly carried out using coffee bean sour water in addition, due to containing a large amount of fat in coffee bean
Class material, it will influence chlorogenic acid and coffee acid are extracted.
The content of the invention
It is an object of the invention to overcome the deficiency of prior art and to provide a kind of rational technology, simple to operate, technique all
Phase is short, coffee bean comprehensive utilization degree is high, rapid extraction chlorogenic acid and caffeinic production technology.
The technical solution adopted by the present invention includes：Degreasing treatment is carried out to coffee bean, is extracted using sour water, cross macroporous absorption
Resin, concentration, ethyl acetate extraction, reversed phase column chromatography, decolorizing with activated carbon, ethyl acetate crystallization and height ethyl alcohol recrystallization, obtain
To chlorogenic acid and caffeic acid sterling.
Therefore, the present invention provides one kind from coffee bean chlorogenic acid extracting and caffeinic method, and specific steps include：
(1) dried coffee bean to 10 mesh~20 mesh is crushed, is added ether to carry out cold soaking and is carried 3~4 hours, its
The weight kg of middle coffee bean is 1 with the volume L ratios of ether:4~10；
(2) ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, and will contain diethyl ether solution is carried out at 40~50 DEG C
It is lower concentrated under reduced pressure, ether is reclaimed, and obtain coffee bean fat；
(3) coffee bean residue is mixed with acetone soln, room temperature extraction, the time is 3~5 hours, wherein coffee bean
The weight kg of residue is 1 with the volume L ratios of acetone soln:5~10, acetone soln is system after acetone and combined
Into acetone volume L is 4 with 0.001mol/L aqueous hydrochloric acid solution volume L ratios：1；
(4) ceramic membrane filter once obtains filtrate, and gained filtrate is concentrated under reduced pressure, and reclaims acetone, and obtain extract solution
Ⅰ；
(5) extract solution I is directly gone up into NKA-9 macroporous absorbent resins, after absorption 30min, with 10% ethanol of 2BV upper prop liquid
Eluant solution, abandons eluent, then is eluted with 20% ethanol water of 3BV upper prop liquid, collects ethanol eluate I, is concentrated into original
The 1/15~1/20 of volume, obtains concentrate I, wherein 20% ethanol water refers to contain in 20% ethanol solution
0.00001mol/L hydrochloric acid；
(6) eluted with 45% ethanol water of 3BV upper prop liquid, collect ethanol eluate II, be concentrated into the 1/ of original volume
10~1/15, concentrate II is obtained, wherein 45% ethanol water refers to containing 0.01mol/L hydrochloric acid in 45% ethanol solution；
(7) concentrate I is decolourized with faintly acid activated carbon, intermittent stirring decolouring 1h, ceramic membrane filter must once be filtered
Liquid, untill the filtrate has been again concentrated into white opacity thing, is cooled to 1~4 DEG C of crystallization 8h, filters to obtain coarse crystallization, then through weight
Caffeic acid sterling is obtained after crystallization；
(8) concentrate II is extracted with the ethyl acetate of two to three times volume, collects upper strata and contain ethyl acetate
Extract, is concentrated under reduced pressure at 40~50 DEG C, reclaims ethyl acetate, and obtain chlorogenic acid pure product.
The filter process is all to use ceramic membrane filter, and fenestra pore size is 0.22 μm.
The concentration process is all to use concentrated under reduced pressure, and temperature control is between 40~55 DEG C.
It is 0.1~5 with the volume L ratios of concentrate I that the weight kg of activated carbon is added in the step (7):1.
10% ethanol water be formulated as with 10mL absolute ethyl alcohols add 90mL water be formulated；20% ethanol solution
Be formulated as with 20mL absolute ethyl alcohols add 80mL water be formulated；Being formulated as of 45% ethanol solution uses 45mL absolute ethyl alcohols
The water of 55mL is added to be formulated.
Technique effect
1st, ungrease treatment can greatly reduce the viscosity of its leaching liquor, improve the rate of filtration, and a large amount of lipids can be obtained again
Material, reduces production cost.
2nd, coffee bean Content of Chlorogenic Acid is high, and the coffee bean chlorogenic acid content of Yunnan Province is up to 14%, and price is low.Make
With coffee bean as the replacement of the medicinal materials such as honeysuckle, folium cortex eucommiae, the utilization ratio of the residues such as coffee bean was both substantially increased, improved
The added value of coffee bean, broken away from the dependence of the medicinal materials such as honeysuckle, folium cortex eucommiae again, and complete incidence graph market is to honeysuckle, the bark of eucommia
The wilderness demand of the medicinal materials such as leaf, extends the medicinal source resource that chlorogenic acid extracts raw material.
3rd, the inventive method is simple to operate, and raw material sources are convenient, can also obtain lot of coffee lipid material.
4th, the reagent used by the present invention is nontoxic, cheap, volume production chemical reagent, using maturation in whole process
The routine techniques that reagent is reclaimed, this greatly reduces to environmental emission discarded object.
Specific embodiment
With reference to specific embodiment, the invention will be further described, and following examples are intended to illustrate rather than
Limitation of the invention further.
Embodiment 1
Dried coffee bean is crushed to 10 mesh~20 mesh, 100KG is weighed and is added 600L ether to carry out cold soaking and carry 3
~4 hours；Ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, and will contain diethyl ether solution subtract at 40~50 DEG C
Pressure concentration, reclaims ether, and obtain coffee bean fat 15kg；Take acetone soln (the 320L acetone of coffee bean residue 70kg and 400L
It is made after mixing with 0.001mol/L aqueous hydrochloric acid solutions of 80L etc.) mixed, room temperature extraction, the time is 3~5 hours；Ceramics
Membrane filtration once obtains filtrate, and gained filtrate is concentrated under reduced pressure, and reclaims acetone, and obtain 60L extract solutions I；Extract solution I is straight
NKA-9 macroporous absorbent resins are connected, after absorption 30min, is eluted with 10% ethanol solution of 2BV upper prop liquid, abandon eluent, then use
20% ethanol water (the containing 0.00001mol/L hydrochloric acid) wash-out of 3BV upper prop liquid, collects the 150L of ethanol eluate I, concentration
To the 1/15 of original volume, 10L concentrates I are obtained；Washed with 45% ethanol water (containing 0.01mol/L hydrochloric acid) of 3BV upper prop liquid
It is de-, the 150L of ethanol eluate II is collected, the 1/10 of original volume is concentrated into, obtain 15L concentrates II；With 2kg faintly acid activated carbons pair
Concentrate I is decolourized, intermittent stirring decolouring 1h, and ceramic membrane filter once obtains filtrate, and the filtrate has been again concentrated into white
Untill muddy thing, 1~4 DEG C of crystallization 8h is cooled to, filters to obtain coarse crystallization, then caffeic acid sterling 1.45kg is obtained after recrystallization；With
The ethyl acetate of two to three times volume is extracted to concentrate II, is collected upper strata and is contained the extract of ethyl acetate, 40~
It is concentrated under reduced pressure at 50 DEG C, reclaims ethyl acetate, and obtain chlorogenic acid pure product 12.68kg.Through HPLC detect, chlorogenic acid sample it is pure
It is 98.5% to spend, and the purity of caffeic acid sample is 98.68%.
Embodiment 2
Dried coffee bean is crushed to 10 mesh~20 mesh, 200KG is weighed and is added 1200L ether to carry out cold soaking and carry
3~4 hours；Ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, and will contain diethyl ether solution is carried out at 40~50 DEG C
It is concentrated under reduced pressure, ether is reclaimed, and obtain coffee bean fat 35kg；Take the acetone soln (480L third of coffee bean residue 100kg and 600L
Ketone and 0.001mol/L aqueous hydrochloric acid solutions of 120L etc. are made after mixing) mixed, room temperature extraction, the time is 3~5 hours；
Ceramic membrane filter once obtains filtrate, and gained filtrate is concentrated under reduced pressure, and reclaims acetone, and obtain 100L extract solutions I；To extract
Liquid I directly goes up NKA-9 macroporous absorbent resins, after absorption 30min, is eluted with 10% ethanol solution of 2BV upper prop liquid, abandons wash-out
Liquid, then eluted with 20% ethanol water (containing 0.00001mol/L hydrochloric acid) of 3BV upper prop liquid, it is collected into 200L ethanol elutions
Liquid I, is concentrated into the 1/20 of original volume, obtains 10L concentrates I；(contain 0.01mol/L with 45% ethanol water of 3BV upper prop liquid
Hydrochloric acid) wash-out, 200L ethanol eluates II are collected, the 1/10 of original volume is concentrated into, obtain 20L concentrates II；Lived with 4kg faintly acids
Property charcoal concentrate I is decolourized, intermittent stirring decolouring 1h, ceramic membrane filter once filtrate, the filtrate is again concentrated to
Untill having white opacity thing, 1~4 DEG C of crystallization 8h is cooled to, filters to obtain coarse crystallization, then caffeic acid sterling is obtained after recrystallization
2.87kg；Concentrate II is extracted with the ethyl acetate of two to three times volume, collects the extraction that ethyl acetate is contained on upper strata
Liquid, is concentrated under reduced pressure at 40~50 DEG C, reclaims ethyl acetate, and obtain chlorogenic acid pure product 18.54kg.Detected through HPLC, green original
The purity of sour sample is 98.67%, and the purity of caffeic acid sample is 98.89%.
Embodiment 3
Dried coffee bean is crushed to 10 mesh~20 mesh, 400KG is weighed and is added 2000L ether to carry out cold soaking and carry
3~4 hours；Ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, and will contain diethyl ether solution is carried out at 40~50 DEG C
It is concentrated under reduced pressure, ether is reclaimed, and obtain coffee bean fat 70kg；Take the acetone soln (960L of coffee bean residue 200kg and 1200L
Acetone and 0.001mol/L aqueous hydrochloric acid solutions of 240L etc. are made after mixing) mixed, room temperature extraction, the time is 3~5 small
When；Ceramic membrane filter once obtains filtrate, and gained filtrate is concentrated under reduced pressure, and reclaims acetone, and obtain 200L extract solutions I；Will
Extract solution I directly goes up NKA-9 macroporous absorbent resins, after absorption 30min, is eluted with 10% ethanol solution of 2BV upper prop liquid, abandons and washes
De- liquid, then eluted with 20% ethanol water (containing 0.00001mol/L hydrochloric acid) of 3BV upper prop liquid, collect ethanol eluate I
400L, is concentrated into the 1/20 of original volume, obtains 20L concentrates I；(contain 0.01mol/ with 45% ethanol water of 3BV upper prop liquid
L hydrochloric acid) wash-out, the 400L of ethanol eluate II is collected, the 1/16 of original volume is concentrated into, obtain 25L concentrates II；Use 5kg faintly acids
Activated carbon decolourizes to concentrate I, intermittent stirring decolouring 1h, and ceramic membrane filter once obtains filtrate, and the filtrate is concentrated again
To having white opacity thing, 1~4 DEG C of crystallization 8h is cooled to, filters to obtain coarse crystallization, then caffeic acid sterling is obtained after recrystallization
5.87kg；Concentrate II is extracted with the ethyl acetate of two to three times volume, collects the extraction that ethyl acetate is contained on upper strata
Liquid, is concentrated under reduced pressure at 40~50 DEG C, reclaims ethyl acetate, and obtain chlorogenic acid pure product 36.35kg.Detected through HPLC, green original
The purity of sour sample is 98.77%, and the purity of caffeic acid sample is 99.15%.
Claims (4)
1. from coffee bean chlorogenic acid extracting and caffeinic method, specific steps include one kind：
(1) dried coffee bean to 10 mesh~20 mesh is crushed, is added ether to carry out cold soaking and is carried 3~4 hours, wherein coffee
The weight kg of coffee beans is 1 with the volume L ratios of ether:4~10；
(2) ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, and will contain diethyl ether solution subtract at 40~50 DEG C
Pressure concentration, reclaims ether, and obtain coffee bean fat；
(3) coffee bean residue is mixed with acetone soln, room temperature extraction, the time is 3~5 hours, wherein coffee bean residue
The volume L ratios of weight kg and acetone soln be 1:5~10, acetone soln is to be made after acetone and combined, third
It is 4 that ketoboidies accumulates L with 0.001mol/L aqueous hydrochloric acid solution volume L ratios：1；
(4) ceramic membrane filter once obtains filtrate, and gained filtrate is concentrated under reduced pressure, and reclaims acetone, and obtain extract solution I；
(5) extract solution I is directly gone up into NKA-9 macroporous absorbent resins, after absorption 30min, with 10% ethanol solution of 2BV upper prop liquid
Wash-out, abandons eluent, then is eluted with 20% ethanol water of 3BV upper prop liquid, collects ethanol eluate I, is concentrated into original volume
1/15~1/20, concentrate I is obtained, wherein 20% ethanol water refers to containing 0.00001mol/L salt in 20% ethanol solution
Acid；
(6) eluted with 45% ethanol water of 3BV upper prop liquid, collect ethanol eluate II, be concentrated into original volume 1/10~
1/15, concentrate II is obtained, wherein 45% ethanol water refers to containing 0.01mol/L hydrochloric acid in 45% ethanol solution；
(7) concentrate I is decolourized with faintly acid activated carbon, intermittent stirring decolouring 1h, ceramic membrane filter once obtains filtrate, will
Untill the filtrate has been again concentrated to white opacity thing, 1~4 DEG C of crystallization 8h is cooled to, filters to obtain coarse crystallization, then after recrystallization
Obtain caffeic acid sterling；
(8) concentrate II is extracted with the ethyl acetate of two to three times volume, collects the extraction that ethyl acetate is contained on upper strata
Liquid, is concentrated under reduced pressure at 40~50 DEG C, reclaims ethyl acetate, and obtain chlorogenic acid pure product.
2. method according to claim 1, wherein filter process is all to use ceramic membrane filter, and fenestra pore size is 0.22 μ
m。
3. method according to claim 1, wherein concentration process be all using concentrated under reduced pressure, temperature control 40~55 DEG C it
Between.
4. method according to claim 1, wherein adds the weight kg of activated carbon and the volume L ratios of concentrate I in step (7)
It is 0.1~5:1.
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| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| CN113336755B (en) * | 2021-06-04 | 2023-03-28 | 北京理工大学 | Method for separating and purifying trigonelline, chlorogenic acid and caffeine |
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| CN101503356B (en) * | 2009-03-25 | 2013-03-13 | 南京工业大学 | Novel method for preparing high-purity chlorogenic acid |
| CN103720830A (en) * | 2013-10-16 | 2014-04-16 | 晨光生物科技集团股份有限公司 | Method for extracting chlorogenic acid composition and coffee bean oil from coffee beans |
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