CN104496815A - Preparation method of medicinal chlorogenic acid - Google Patents
Preparation method of medicinal chlorogenic acid Download PDFInfo
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- CN104496815A CN104496815A CN201410696450.9A CN201410696450A CN104496815A CN 104496815 A CN104496815 A CN 104496815A CN 201410696450 A CN201410696450 A CN 201410696450A CN 104496815 A CN104496815 A CN 104496815A
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- C07—ORGANIC CHEMISTRY
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C07—ORGANIC CHEMISTRY
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention provides a preparation method of medicinal chlorogenic acid, wherein the preparation method comprises the following steps: a, carrying out water phase treatment on a sample; b, freezing; c, thawing and filtering; d, carrying out organic phase treatment on the filter residue; e, concentrating and crystallizing; f, according to a difference of the contents of chlorogenic acid in the sample, selecting the repeating times of the a-e steps; and g, drying. A chlorogenic acid extract is separated and purified by the method, water-soluble impurities and fat-soluble impurities in the extract can be better removed, and thus the impurity content of the final product meets the medicinal requirements; at the same time, the method has the advantages of simple operation, recyclable organic solvent and low cost, is suitable for further separation and purification of a chlorogenic acid extract extracted by all kinds of methods, and is especially suitable for the preparation of the medicinal chlorogenic acid.
Description
Technical field
The present invention relates to a kind of preparation method of medicinal chlorogenic acid.
Background technology
Chlorogenic acid has anti-microbial effect more widely, 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.The separation purification method of current report chlorogenic acid is more, as: application number: CN201010558366 denomination of invention: the production method of Freeze Concentration crystalline chlorogenic acid, the invention discloses a kind of production method of chlorogenic acid crystallization, belong to the novel method that natural product extraction liquid is concentrated, can be used for the Crystallization Separation of the concentrated and compound of aqueous solution in Separation of Natural Products purge process.The present invention is by 50% methyl alcohol solution of chlorogenic acid 0 DEG C of crystallization, filtering for crystallizing body, and crystalline mother solution is freezing icing at-50 DEG C, is then taken out by ice, is broken into Powdered by ice shaver.Ice end is delivered on separating centrifuge and carry out centrifugation, obtain the methyl alcohol solution of chlorogenic acid of high density.Then in solution, add water to methanol concentration is 50% methyl alcohol solution of chlorogenic acid.This solution is placed in crystallization under 0 DEG C of condition, fractional crystallization body, vacuum lyophilization, obtains the chlorogenic acid that content is more than 98%.Application number: CN201210543580, denomination of invention: a kind of method preparing chlorogenic acid from leaf of Lonicera hypoglauca Miq., a kind of production technique simultaneously extracting asperuloside and chlorogenic acid from Folium Eucommiae.It is with the raw material of the Folium Eucommiae of drying, adopts heating in water bath extractions, upper prop, wash-out, concentrates, the technical process such as dynamic extraction, crystallization, recrystallization obtains asperuloside sterling; Chlorogenic acid is extracted after being merged by the thick paste stayed after the acetone mother liquor concentrations stayed after crystallization and dynamic extraction again.Application number: CN201010135116, denomination of invention: a kind of method of preparing chlorogenic acid from eucommia leaves fine work, the present invention relates to a kind of method of preparing chlorogenic acid from eucommia leaves fine work, deionized water soak at room temperature is adopted to extract, squeezing (or centrifugal), the enrichment of macroporous absorption column chromatography, ethyl acetate extraction, the technical process of deionized water recrystallization.
Conventional chlorogenic acid process for purification also has: resin column chromatography, Thin-layer chromatography, gel chromatography, high performance liquid chromatography, crystallization and recrystallization method etc.Resin column chromatography, the method can enriching and purifying chlorogenic acid, but sample purity and impurity cannot be made to meet medicinal requirements by means of only the method; Thin-layer chromatography, the method can make chlorogenic acid be well separated with flavonoid, can obtain the chlorogenic acid of higher degree by purifying, but troublesome poeration, elution time is long, cost is high, and material not easily regenerates, and industrialization investment is larger; Gel chromatography, can obtain high-purity chlorogenic acid by the method, but because gel is expensive, product yield is low, is difficult to realize suitability for industrialized production; High performance liquid chromatography, the method can obtain the chlorogenic acid of higher degree, but because technical requirements is high, yield poorly, still rest on laboratory stage at present; Crystallization and recrystallization are conventional process for purification, the method energy enriching and purifying high-purity chlorogenic acid, but usually adopt single solvent to carry out crystallization and recrystallization purifying process, the impurity specific aim of purifying removing is stronger, separation and purification cannot be carried out to the impurity of opposed polarity simultaneously, comparatively large to extract selectivity, the extract that different process is prepared cannot be widely used in.Part Research Literature is had to report, adopt the process for purification of double solvents crystallization and recrystallization, the object that opposed polarity impurity reaches purifying is removed by the kind and ratio that change double solvents, the method effectively can remove the impurity of the opposed polarity in extract, but owing to there is very large difficulty during double solvents recycling, have some limitations equally, simultaneously in product because remaining double solvents, there is very big potential safety hazard.
Summary of the invention
Technical scheme of the present invention there is provided a kind of preparation method of chlorogenic acid.
The invention provides a kind of preparation method of medicinal chlorogenic acid, it comprises the steps:
A, sample water process mutually: sample purified water is mixed with the solution containing chlorogenic acid 20mg/ml-2000mg/ml, filter; Wherein sample goes out by Folium Eucommiae extraction and isolation the extract that chlorogenic acid content is not less than 60%; Preparation temperature is not higher than 60 DEG C;
B, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
C, filtration of thawing: the ice cube of freezing gained is thawed under 5-60 DEG C of condition, and keep thawing solution temperature not higher than 5 DEG C, filter;
D, the process of filter residue organic phase: will filter gained filter residue, and fully dissolve with organic solvent, filter; Wherein organic solvent is the one in the middle of methyl acetate, ethyl acetate, propyl acetate and butylacetate; Solvent temperature is not higher than 60 DEG C;
E, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitate generation on a small quantity until have, leave standstill crystallization; Thickening temperature is not higher than 60 DEG C, and vacuum tightness is not less than 0.04Mp;
The otherness of the content of f, per sample Content of Chlorogenic Acid, selects a-e step multiplicity; When extractive content is 60-80%, repetition twice operation of a-e step; When extractive content is 80-90%, the repetition single job of a-e step; When extractive content is more than 90%, without the need to repetitive operation;
G, drying: after being filtered by xln, under cold condition, carry out drying; Drying temperature, can be dry under normal pressure or condition of negative pressure not higher than 60 DEG C.
Further preferably, it comprises the steps:
A, sample water process mutually: sample purified water is mixed with the solution containing chlorogenic acid 500mg/ml, filter; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 90%; Preparation temperature is 40 DEG C;
B, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
C, filtration of thawing: the ice cube of freezing gained is thawed under 25 DEG C of conditions, and keep thawing solution temperature not higher than 5 DEG C, filter;
D, the process of filter residue organic phase: will filter gained filter residue, and fully dissolve with organic solvent, filter; Wherein organic solvent is ethyl acetate; Solvent temperature is 60 DEG C;
E, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitate generation on a small quantity until have, leave standstill crystallization; Thickening temperature is 60 DEG C, and vacuum tightness is 0.08Mp;
F, drying: after being filtered by xln, under cold condition, carry out drying; Drying temperature is 60 DEG C, dry under condition of normal pressure.
Present invention also offers the chlorogenic acid that the method prepares.
Wherein, chlorogenic acid content is greater than 98%, containing one to six kind of related substance, comprising having 5-CQ, 4-vinyl pyrocatechol, coffic acid, 4-caffeoyl-quinic acid, 3-coumaroyl guinic acid, chlorogenic acid methide, content is all below 0.5%.
The method that the present invention adopts water to be combined with organic solvent, utilizes the otherness of chlorogenic acid and water-soluble impurity solubleness in differing temps water, by the water-soluble impurity in the freezing heavy molten method removing extract of aqueous phase; The otherness of recycling chlorogenic acid and oil-soluble impurities solubleness in organic solvent, by removing the oil-soluble impurities in extract to the method for organic solution condensing crystal.By the solvent of these two kinds of opposed polarities to the separation and purification of chlorogenic acid extract, the water-soluble impurity in extract and oil-soluble impurities can be removed well, make the foreign matter content of the finished product meet medicinal requirements; The method is simple to operate simultaneously, and organic solvent recoverable, cost is low, is applicable to various method and extracts the further separation and purification of chlorogenic acid extract obtained, be particularly useful for the preparation of medicinal chlorogenic acid.
Embodiment
The preparation method of the medicinal chlorogenic acid of embodiment 1 the present invention
1, sample water processes mutually: sample purified water is mixed with the solution containing chlorogenic acid 500mg/ml, filters; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 90%; Preparation temperature is 40 DEG C.
2, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
3, to thaw filtration: the ice cube of freezing gained is thawed under 25 DEG C of conditions, and keeps thawing solution temperature not higher than 5 DEG C, filter;
4, filter residue organic phase process: will filter gained filter residue, and fully dissolve with organic solvent, filters; Wherein organic solvent is ethyl acetate; Solvent temperature is 60 DEG C;
5, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitates generation on a small quantity until have, leaves standstill crystallization; Thickening temperature is 60 DEG C, and vacuum tightness is 0.08Mp;
6, dry: after being filtered by xln, under cold condition, to carry out drying; Drying temperature is 60 DEG C, dry under condition of normal pressure.
The preparation method of the medicinal chlorogenic acid of embodiment 2 the present invention
1, sample water processes mutually: sample purified water is mixed with the solution containing chlorogenic acid 800mg/ml, filters; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 60%; Preparation temperature is 50 DEG C;
2, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
3, to thaw filtration: the ice cube of freezing gained is thawed under 10 DEG C of conditions, and keeps thawing solution temperature not higher than 5 DEG C, filter;
4, filter residue organic phase process: will filter gained filter residue, and fully dissolve with organic solvent, filters; Wherein organic solvent is propyl acetate; Solvent temperature is 60 DEG C;
5, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitates generation on a small quantity until have, leaves standstill crystallization; Thickening temperature is 60 DEG C, and vacuum tightness is 0.07Mp;
6, a-e step repeats twice operation in accordance with the law;
7, dry: after being filtered by xln, under cold condition, to carry out drying; Drying temperature is 60 DEG C, dry under condition of normal pressure.
The preparation method of the medicinal chlorogenic acid of embodiment 3 the present invention
1, sample water processes mutually: sample purified water is mixed with the solution containing chlorogenic acid 20mg/ml, filters; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 85%; Preparation temperature is 20 DEG C;
2, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
3, to thaw filtration: the ice cube of freezing gained is thawed under 5 DEG C of conditions, and keeps thawing solution temperature not higher than 5 DEG C, filter;
4, filter residue organic phase process: will filter gained filter residue, and fully dissolve with organic solvent, filters; Wherein organic solvent is methyl acetate; Solvent temperature is 20 DEG C;
5, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitates generation on a small quantity until have, leaves standstill crystallization; Thickening temperature is 40 DEG C, and vacuum tightness is 0.04Mp;
6, a-e step repeats single job in accordance with the law;
7, dry: after being filtered by xln, under cold condition, to carry out drying; Drying temperature is 40 DEG C, dry under condition of normal pressure.
The preparation method of the medicinal chlorogenic acid of embodiment 4 the present invention
1, sample water processes mutually: sample purified water is mixed with the solution containing chlorogenic acid 100mg/ml, filters; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 72%; Preparation temperature is 30 DEG C;
2, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
3, to thaw filtration: the ice cube of freezing gained is thawed under 60 DEG C of conditions, and keeps thawing solution temperature not higher than 5 DEG C, filter;
4, filter residue organic phase process: will filter gained filter residue, and fully dissolve with organic solvent, filters; Wherein organic solvent is butylacetate; Solvent temperature is 60 DEG C;
5, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitates generation on a small quantity until have, leaves standstill crystallization; Thickening temperature is 60 DEG C, and vacuum tightness is 0.09Mp;
6, a-e step repeats twice operation in accordance with the law;
7, dry: after being filtered by xln, under cold condition, to carry out drying; Drying temperature is 60 DEG C, dry under condition of negative pressure.
The preparation method of the medicinal chlorogenic acid of embodiment 5 the present invention
1, sample water processes mutually: sample purified water is mixed with the solution containing chlorogenic acid 2000mg/ml, filters; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 68%; Preparation temperature is 60 DEG C;
2, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
3, to thaw filtration: the ice cube of freezing gained is thawed under 60 DEG C of conditions, and keeps thawing solution temperature not higher than 5 DEG C, filter;
4, filter residue organic phase process: will filter gained filter residue, and fully dissolve with organic solvent, filters; Wherein organic solvent is ethyl acetate; Solvent temperature is 50 DEG C;
5, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitates generation on a small quantity until have, leaves standstill crystallization; Thickening temperature is 50 DEG C, and vacuum tightness is 0.05Mp;
6, a-e step repeats twice operation in accordance with the law;
7, dry: after being filtered by xln, under cold condition, to carry out drying; Drying temperature is 40 DEG C, dry under condition of negative pressure
The preparation method of the medicinal chlorogenic acid of embodiment 6 the present invention
1, sample water processes mutually: sample purified water is mixed with the solution containing chlorogenic acid 1500mg/ml, filters; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 95%; Preparation temperature is 60 DEG C;
2, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
3, to thaw filtration: the ice cube of freezing gained is thawed under 60 DEG C of conditions, and keeps thawing solution temperature not higher than 5 DEG C, filter;
4, filter residue organic phase process: will filter gained filter residue, and fully dissolve with organic solvent, filters; Wherein organic solvent is propyl acetate; Solvent temperature is 60 DEG C;
5, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitates generation on a small quantity until have, leaves standstill crystallization; Thickening temperature is 60 DEG C, and vacuum tightness is 0.08Mp;
6, dry: after being filtered by xln, under cold condition, to carry out drying; Drying temperature is 60 DEG C, dry under condition of negative pressure
The quality of the medicinal chlorogenic acid of embodiment 7 embodiment of the present invention 1-6
The detection method of content is:
Chromatographic condition and system suitability octadecyl silane are weighting agent; With 0.1% formic acid solution-acetonitrile (92:8) for moving phase; Determined wavelength 215nm; Number of theoretical plate calculates should be not less than 3000 by chlorogenic acid peak, and the resolution at chlorogenic acid peak and other impurities peak should meet the requirements;
It is appropriate, accurately weighed that assay method gets this product, and add moving phase and make every 1ml about containing the solution of 10 μ g, as need testing solution, precision measures 20 μ l injection liquid chromatographies, record color atlas; Separately get chlorogenic acid reference substance appropriate, accurately weighed, add moving phase and make the solution of every 1ml containing 10 μ g, be measured in the same method; By external standard method with calculated by peak area, to obtain final product;
The detection method of impurity is:
Get this product appropriate, accurately weighed, add moving phase and make the solution of every 1ml containing 0.5mg, as need testing solution; Get need testing solution 1ml to put in 100ml measuring bottle, add moving phase and be diluted to scale, in contrast solution; Separately get coffic acid reference substance appropriate, accurately weighed, add moving phase and make the solution containing 2 μ g in every 1ml, product solution in contrast; According to the chromatographic condition under assay item, get contrast solution 20 μ l injection liquid chromatography, regulate detection sensitivity, principal constituent chromatographic peak peak height is made to be about 20% of full range, precision measures each 20 μ l of need testing solution, contrast solution and reference substance solution again, injection liquid chromatography respectively, record color atlas is to 3 times of principal constituent peak retention time; If any coffic acid impurity peaks in need testing solution color atlas, calculate by external standard method; If any other impurity peaks, calculate by Self-control method.
The quality of medicinal chlorogenic acid in each embodiment of table 1
Claims (4)
1. a preparation method for medicinal chlorogenic acid, it comprises the steps:
A, sample water process mutually: sample purified water is mixed with the solution containing chlorogenic acid 20mg/ml-2000mg/ml, filter; Wherein sample goes out by Folium Eucommiae extraction and isolation the extract that chlorogenic acid content is not less than 60%; Preparation temperature is not higher than 60 DEG C;
B, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
C, filtration of thawing: the ice cube of freezing gained is thawed under 5-60 DEG C of condition, and keep thawing solution temperature not higher than 5 DEG C, filter;
D, the process of filter residue organic phase: will filter gained filter residue, with organic solvent dissolution, filter, obtain organic solution; Wherein organic solvent is the one in the middle of methyl acetate, ethyl acetate, propyl acetate and butylacetate; Solvent temperature is not higher than 60 DEG C;
E, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, until there is precipitation to produce, leave standstill crystallization; Thickening temperature is not higher than 60 DEG C, and vacuum tightness is not less than 0.04Mp;
The otherness of the content of f, per sample Content of Chlorogenic Acid, selects a-e step multiplicity; When extractive content is 60-80%, repetition twice operation of a-e step; When extractive content is 80-90%, the repetition single job of a-e step; When extractive content is more than 90%, without the need to repetitive operation;
G, drying: after being filtered by xln, under cold condition, carry out drying; Drying temperature, can be dry under normal pressure or condition of negative pressure not higher than 60 DEG C.
2. preparation method according to claim 1, is characterized in that: it comprises the steps:
A, sample water process mutually: sample purified water is mixed with the solution containing chlorogenic acid 500mg/ml, filter; Wherein sample goes out by extraction and isolation in Folium Eucommiae the extract that chlorogenic acid content is 90%; Preparation temperature is 40 DEG C;
B, freezing: by freezing in less than 0 DEG C for the filtrate of filtering gained, until filtrate is completely freezing;
C, filtration of thawing: the ice cube of freezing gained is thawed under 25 DEG C of conditions, and keep thawing solution temperature not higher than 5 DEG C, filter;
D, the process of filter residue organic phase: will filter gained filter residue, and fully dissolve with organic solvent, filter; Wherein organic solvent is ethyl acetate; Solvent temperature is 60 DEG C;
E, condensing crystal: organic solution is concentrated under low-temperature negative-pressure condition, precipitate generation on a small quantity until have, leave standstill crystallization; Thickening temperature is 60 DEG C, and vacuum tightness is 0.08Mp;
F, drying: after being filtered by xln, under cold condition, carry out drying; Drying temperature is 60 DEG C, dry under condition of normal pressure.
3. the chlorogenic acid for preparing of the method for claim 1 or 2.
4. chlorogenic acid according to claim 3, it is characterized in that: chlorogenic acid purity is greater than 98%, containing one to six kind of related substance, comprising having 5-CQ, 4-vinyl pyrocatechol, coffic acid, 4-caffeoyl-quinic acid, 3-coumaroyl guinic acid, chlorogenic acid methide, content is all below 0.5%.
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| WO2016082122A1 (en) * | 2014-11-26 | 2016-06-02 | 四川九章生物科技有限公司 | Preparation method for medicinal chlorogenic acid |
| CN107879937A (en) * | 2017-10-24 | 2018-04-06 | 四川九章生物科技有限公司 | A kind of new crystal of chlorogenic acid and preparation method thereof |
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| CN102040520A (en) * | 2010-11-15 | 2011-05-04 | 浙江工业大学 | Method for separating and purifying chlorogenic acid from eucommia bark leaves |
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| WO2016082122A1 (en) * | 2014-11-26 | 2016-06-02 | 四川九章生物科技有限公司 | Preparation method for medicinal 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 |
| CN107879937A (en) * | 2017-10-24 | 2018-04-06 | 四川九章生物科技有限公司 | A kind of new crystal of chlorogenic acid and preparation method thereof |
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