CN107857699A - A kind of technique that shikimic acid is extracted from anise - Google Patents
A kind of technique that shikimic acid is extracted from anise Download PDFInfo
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- CN107857699A CN107857699A CN201711104025.6A CN201711104025A CN107857699A CN 107857699 A CN107857699 A CN 107857699A CN 201711104025 A CN201711104025 A CN 201711104025A CN 107857699 A CN107857699 A CN 107857699A
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- C—CHEMISTRY; METALLURGY
- 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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- C—CHEMISTRY; METALLURGY
- 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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- 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
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
- C08F251/02—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof on to cellulose or derivatives thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2265—Oxides; Hydroxides of metals of iron
- C08K2003/2272—Ferric oxide (Fe2O3)
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
The invention discloses a kind of technique that shikimic acid is extracted from anise, crude extract is obtained including extracting shikimic acid from anise using high-pressure homogenization method, then prepared magnetic molecularly imprinted polymer is used to adsorb the shikimic acid in crude extract, so as to simply and efficiently realize the separation of shikimic acid.Anistree shikimic acid is extracted from anise using the method for the present invention, it is environmentally friendly, recovery rate is high, good product quality, it is with short production cycle, easy to operate, cost is relatively low, is adapted to industrialized production.
Description
Technical field
The present invention relates to a kind of extraction process, more particularly to a kind of technique that shikimic acid is extracted from anise.
Background technology
Anise is also known as Chinese anise, anise, aniseed, scientific name Illiciumverum, is important " the medicine food of south China
It is homologous " economic tree, one kind of Dicotyledoneae Magnoliidae Winteraceae Illicium, mainly originate in Guangxi, Yunnan, Fujian
South, West of Guangdong.Chinese anise fruit can be cooked flavoring, and leaf, fruit can steam aromatic oil, claim oil of badian, and its content is generally
5%~12%, fennel oil can be applied to manufacture the food industry such as julapium；And the perfume (or spice) of toothpaste processed, perfumed soap, perfume, cosmetics
Material；Modulated bactericide, strong kidney agent, galactopoietic etc. in medical industries.In addition, the shikimic acid extracted in its fruit is also mesh
The specific medicament phosphoric acid Ao Si meter of the anti-H5N1 subtype highly pathogenic avian influenzas of an only synthesis of the international raw Organisation recommendations of Qian Bei
The key component of Wei (oseltamivirphosphate) (Tamiflu).
Shikimic acid is also known as shihimic acid, molecular formula C7H10O5, relative molecular weight 174.15, scientific name is 3,4,5- tri- hydroxyls
Base -1- cyclohexene -1- carboxylic acids (3,4,5-trihydroxy-l-cyclohexen-1-carboxylicacid), it is white fine
Powder, gas is micro-, acrid flavour acid, soluble in water, and hard to tolerate in chloroform, benzene and petroleum ether, fusing point is 185 DEG C, and optical activity is -180.Thick grass
There are three hydroxyls, a carboxyl, a double bond in acid molecular structures, there is chiral isomer.It can be into ester, can also be into
Salt.Shikimic acid is the intermediate of interior, the metabolic compound of synthesising biological body, and synthesizes many alkaloids, ArAA
With indole derivatives, the raw material of chiral drug (such as antiviral agent).Shikimic acid has analgesia, antibacterial, anti-platelet aggregation, anti-swollen
Knurl, antithrombus formation and anti-cerebral ischemia etc. act on.Shikimic acid is the important source material for being used to manufacture medicine " Tamiflu ", has expert to claim
" Tamiflu " is the unique weapon for tackling bird flu in the world at present.
At present, extracting the method for shikimic acid has heat reflow method, surname extraction, ultrasonic extraction, microwave-assisted
Deng.Traditional heat reflow method extraction time length, energy consumption is big, and recovery rate is relatively low.Sound and vibration intensity is relatively low during ultrasonic extraction；Microwave
The change and destruction of some organic structures in sample may be caused during extraction under hot conditions, and before extract solution is taken out also
Need longer cool time.
In a word, the extraction purification report on shikimic acid is existing a lot, but so far still without find a kind of energy consumption it is low, when
Between short, process cleans, technique is simple and the method for good separating effect, therefore develop a kind of new and effective shikimic acid extraction and purification
Technology is highly desirable.
The content of the invention
The defects of it is an object of the invention to overcome prior art, there is provided a kind of shikimic acid yield is high, utilizes magnetic molecule
Imprinted templates extraction be it is a kind of it is easy to operate, economical and practical, be suitable for the isolation technics that industrialized production uses.
In order to solve the above-mentioned technical problem, the present invention provides a kind of technique that shikimic acid is extracted from anise, and its step is such as
Under：
1) shikimic acid extract solution is prepared：Dry anise is carried out to crushed 40 mesh sieves, a certain amount of distillation is added after spy
Water is simultaneously stirred, and high-pressure homogenization is handled 1~3 hour, obtains homogenate；Then in the case where power output is 600W microwave condition
Processing 6~10 minutes, extracted 2~5 times under the conditions of being 70~90 DEG C in temperature with ethanol, merge extract solution；
2) magnetic molecularly imprinted polymer is prepared：Using suspension polymerization, using shikimic acid as template molecule, what oleic acid was modified
Nanometer Fe2O3Particle is magnetic component, and tetravinyl pyridine is function monomer, and the carboxyethyl cellulose aqueous solution is dispersant, diformazan
Base acrylic acid glycol ester is that crosslinking agent prepares anistree shikimic acid magnetic molecularly imprinted polymer；
3) magnetic molecularly imprinted polymer for obtaining step 2) is devised a stratagem with the extract solution that step 1) obtains according to one
Amount is than mixing, vibration absorption 1~3 hour；Then the magnetic molecularly imprinted polymerization of anistree shikimic acid will be adsorbed with by Magneto separate
Thing is come out from liquid phase separation, and the alcohol mixeding liquid that percent by volume is 50~70%, vibration elution are added in magnetropism adsorbent
30~60 minutes, after Magneto separate, collect eluent；It is concentrated and be dried under reduced pressure, obtain shikimic acid.
In step 1), the dosage of distilled water is 1~10 times of anistree powder weight；The pressure of high-pressure homogenization processing is
60MPa, time are 2 hours.
Molecular imprinting technology (Molecularimprintingtechnology, MIT) is also known as molecular imprinting technique, category
An interdisciplinary field between polymer chemistry, material science, biochemistry, analytical chemistry etc..Molecular imprinting technology
It is to obtain the polymer matched completely with a certain molecule (commonly referred to as template molecule) on space structure and binding sites
Test technology of preparing.Molecularly imprinted polymer (Molecularimprintingpolymer, MIPs) refer to using target molecule as
Template molecule, by the functionalized polymer monomer with complementary structure by way of covalently or non-covalently with template molecule knot
Close, add crosslinking agent and carry out polymerisation, the one kind formed after template molecule is extracted after the completion of reaction has fixed cavitation
Size and shape and the cross-linked polymer for having determination arranging functional group.It is so rapid why molecular imprinting technology develops, mainly
It is because it has precordainment (Predetermination), identity (Recognition) and practicality
(Practicability).Suspension polymerization is a kind of common method for preparing ball-type molecularly imprinted polymer at present.In recent years,
Many scholars prepare molecular blotting polymer microsphere using various novel dispersants and achieve new progress, and its reaction system is general
It is made up of monomer, fat-soluble initiators, dispersant and water.Building-up process is first to be dissolved monomer with organic solvent, be added to dissolved with
In stable water or other highly polar solvents, high-speed stirred obtains suspension, then adds initiator, triggers polymerization to be divided
Sub- imprinted polymer microballoon.
In step 2), the ratio between template molecule, function monomer and crosslinking agent is preferably 1：4：16；
In step 3), the magnetic molecularly imprinted polymer obtains part by weight as 0.1~0.3 with extract solution：1~5；It is described
Magnetic molecularly imprinted polymer can be recycled after drying after elution.
Advantages of the present invention is as follows：
In the present invention, take high-pressure homogenization to extract anistree shikimic acid, in a short time the active ingredient in anise is existed
Quickly it is fully dissolved out from water under high pressure, reaction condition is gentle, is advantageous to the structural defence to active material, and will not introduce
New organic impurities, ensure the security of final products, also reduce environmental pollution；Meanwhile magnetic template molecule is taken to thick grass
Acid carries out selective absorption, simply and efficiently realizes the separation of anistree shikimic acid.
In a word, anistree shikimic acid is extracted from anise using the inventive method, simple efficient, environmentally friendly, recovery rate
Height, good product quality is with short production cycle, easy to operate, cost is relatively low, is easy to industrialization, has good popularizing application prospect.
Embodiment
The technical scheme in the embodiment of the present invention is clearly and completely described below, it is clear that described embodiment
Only part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, the common skill in this area
The every other embodiment that art personnel are obtained on the premise of creative work is not made, belong to the model that the present invention protects
Enclose.
【Embodiment 1】
1) shikimic acid extract solution is prepared：Anise is crushed, crosses 60 mesh sieves, distilled water is added and obtains solid content as 10%
Aqueous dispersions；Under conditions of pressure 100MPa, the aqueous dispersions are subjected to high-pressure homogenization and handled 30 minutes, are homogenized
Liquid；The homogenate is handled 3 minutes in the case where power output is 600W microwave condition, in temperature is 70~90 DEG C of bars with ethanol
Extracted 4 times under part, merge extract solution；
2) magnetic molecularly imprinted polymer is prepared：Using suspension polymerization, using shikimic acid as template molecule, what oleic acid was modified
Nanometer Fe3O4Particle is magnetic component, and tetravinyl pyridine is function monomer, and the carboxyethyl cellulose aqueous solution is dispersant, diformazan
Base acrylic acid glycol ester is that crosslinking agent prepares anistree shikimic acid magnetic molecularly imprinted polymer.
3) extract solution that the magnetic molecularly imprinted polymer for obtaining step 2) obtains with step 1) is according to weight ratio
For 0.1:1 mixing, vibration absorption 2 hours；Then the magnetic molecularly imprinted polymerization of anistree shikimic acid will be adsorbed with by Magneto separate
Thing is come out from liquid phase separation, and the alcohol mixeding liquid that percent by volume containing acetic acid is 50% is added in magnetropism adsorbent, and vibration is washed
It is de- 30~60 minutes, after Magneto separate, collect eluent；It is concentrated and be dried under reduced pressure, obtain shikimic acid.Detected through HPLC, product
Purity is thick grass acid content 96.8%.
【Embodiment 2】
1) shikimic acid extract solution is prepared：Anise is crushed, crosses 60 mesh sieves, adds distilled water to stir 60 minutes, consolidate
Content is 5% aqueous dispersions；Under conditions of pressure 60MPa, the aqueous dispersions are subjected to high-pressure homogenization and handled 60 minutes,
Obtain homogenate；By the homogenate power output be 600W microwave condition under handle 3 minutes, with ethanol temperature be 90
Extracted 5 times under the conditions of DEG C, merge extract solution；
2) magnetic molecularly imprinted polymer is prepared：Using suspension polymerization, using shikimic acid as template molecule, acid is modified to be received
Rice Fe2O3Particle is magnetic component, and tetravinyl pyridine is function monomer, and the carboxyethyl cellulose aqueous solution is dispersant, dimethyl
Acrylic acid glycol ester is that crosslinking agent prepares anistree shikimic acid magnetic molecularly imprinted polymer.
3) extract solution that the magnetic molecularly imprinted polymer for obtaining step 2) obtains with step 1) is according to weight ratio
For 0.3:1 mixing, vibration absorption 2 hours；Then the magnetic molecularly imprinted polymerization of anistree shikimic acid will be adsorbed with by Magneto separate
Thing is come out from liquid phase separation, and the alcohol mixeding liquid that percent by volume containing acetic acid is 50~70% is added in magnetropism adsorbent, is shaken
Swing elution 30~60 minutes, after Magneto separate, collect eluent；It is concentrated and be dried under reduced pressure, obtain shikimic acid.Detected through HPLC,
Product purity is thick grass acid content 97.9%.
The present invention has the advantages that：
The present invention takes high-pressure homogenization to extract anistree shikimic acid, causes the active ingredient in anise in high pressure in a short time
Under be quickly fully dissolved out from water, reaction condition is gentle, is advantageous to the structural defence to active material, and will not introduce new
Organic impurities, ensure the security of final products, also reduce environmental pollution；Meanwhile magnetic template molecule is taken to enter shikimic acid
Row selective absorption, simply and efficiently realize the separation of anistree shikimic acid.
In a word, anistree shikimic acid is extracted from anise using the inventive method, simple efficient, environmentally friendly, recovery rate
Height, good product quality is with short production cycle, easy to operate, cost is relatively low, is easy to industrialization, has good popularizing application prospect.
Described above has fully disclosed the embodiment of the present invention.It is pointed out that it is familiar with the field
Scope of the technical staff to any change that the embodiment of the present invention is done all without departing from claims of the present invention.
Correspondingly, the scope of claim of the invention is also not limited only to previous embodiment.
Claims (5)
1. a kind of technique that shikimic acid is extracted from anise, its step are as follows：
1) shikimic acid extract solution is prepared：Dry anise is carried out to crushed 40 mesh sieves, then adds a certain amount of distilled water simultaneously
Stir, high-pressure homogenization is handled 1~3 hour, obtains homogenate；Then handled in the case where power output is 600W microwave condition
6~10 minutes, extracted 2~5 times under the conditions of being 70~90 DEG C in temperature with ethanol, merge extract solution；
2) magnetic molecularly imprinted polymer is prepared：Using suspension polymerization, using shikimic acid as template molecule, the nanometer of oleic acid modification
Fe2O3Particle is magnetic component, and tetravinyl pyridine is function monomer, and the carboxyethyl cellulose aqueous solution is dispersant, dimethyl propylene
Olefin(e) acid glycol ester is that crosslinking agent prepares anistree shikimic acid magnetic molecularly imprinted polymer；
3) magnetic molecularly imprinted polymer for obtaining step 2) measures ratio with the extract solution that step 1) obtains according to certain
Mixing, vibration absorption 1~3 hour；Then by Magneto separate will be adsorbed with the magnetic molecularly imprinted polymer of anistree shikimic acid from
Liquid phase separation is come out, and percent by volume is added in magnetropism adsorbent as 50~70% alcohol mixeding liquid, and vibration elution 30~
60 minutes, after Magneto separate, collect eluent；It is concentrated and be dried under reduced pressure, obtain shikimic acid.
2. the technique according to claim 1 that shikimic acid is extracted from anise, it is characterised in that the high-pressure homogenization processing
Pressure be 60MPa, the time is 1 hour.
3. the technique according to claim 1 that shikimic acid is extracted from anise, it is characterised in that in step 2), template point
Ratio between son, function monomer and crosslinking agent is preferably 1：4：16.
4. the technique according to claim 1 that shikimic acid is extracted from anise, it is characterised in that in step 3), the magnetic
Property molecularly imprinted polymer and extract solution part by weight be 0.1~0.3：1~5.
5. the technique according to claim 1 that shikimic acid is extracted from anise, it is characterised in that described magnetic molecularly imprinted
Polymer can be recycled after drying after elution.
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| CN201711104025.6A CN107857699A (en) | 2017-11-10 | 2017-11-10 | A kind of technique that shikimic acid is extracted from anise |
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| CN201711104025.6A CN107857699A (en) | 2017-11-10 | 2017-11-10 | A kind of technique that shikimic acid is extracted from anise |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108272848A (en) * | 2018-04-18 | 2018-07-13 | 佛山市飞程信息技术有限公司 | A kind of extraction process of Maca extract |
| CN108552370A (en) * | 2018-04-18 | 2018-09-21 | 佛山市飞程信息技术有限公司 | A method of extraction tea polyphenols |
| CN112973457A (en) * | 2021-02-01 | 2021-06-18 | 江苏大学 | Preparation method of cellulose acetate boron affinity imprinted membrane and application of cellulose acetate boron affinity imprinted membrane in selective separation of shikimic acid |
| CN114618449A (en) * | 2022-04-19 | 2022-06-14 | 重庆迈德凯医药有限公司 | Oxalic acid adsorbent, preparation method and application thereof |
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| WO2007138607A1 (en) * | 2006-05-25 | 2007-12-06 | Iyer Sankar V | Method for obtaining shikimic acid |
| CN102659982A (en) * | 2012-05-24 | 2012-09-12 | 国际竹藤中心 | Flavone magnetic molecularly imprinted polymer, preparation of flavone magnetic molecularly imprinted polymer, and application of flavone magnetic molecularly imprinted polymer to bamboo-leaf flavone separation |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108272848A (en) * | 2018-04-18 | 2018-07-13 | 佛山市飞程信息技术有限公司 | A kind of extraction process of Maca extract |
| CN108552370A (en) * | 2018-04-18 | 2018-09-21 | 佛山市飞程信息技术有限公司 | A method of extraction tea polyphenols |
| CN112973457A (en) * | 2021-02-01 | 2021-06-18 | 江苏大学 | Preparation method of cellulose acetate boron affinity imprinted membrane and application of cellulose acetate boron affinity imprinted membrane in selective separation of shikimic acid |
| CN114618449A (en) * | 2022-04-19 | 2022-06-14 | 重庆迈德凯医药有限公司 | Oxalic acid adsorbent, preparation method and application thereof |
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