CN110092811A - A kind of preparation method of betulin - Google Patents
A kind of preparation method of betulin Download PDFInfo
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- CN110092811A CN110092811A CN201910483387.3A CN201910483387A CN110092811A CN 110092811 A CN110092811 A CN 110092811A CN 201910483387 A CN201910483387 A CN 201910483387A CN 110092811 A CN110092811 A CN 110092811A
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- betulin
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- white solid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Abstract
A kind of preparation method of betulin, it is related to betulin preparation, at high cost the invention aims to solve existing betulin extracting method there are complicated for operation, pollution is big, Japanese birch bark is extracted with alcohol reflux, then is concentrated with dichloromethane solution by the problem of being not easy to industrialized production, it is flowed back with acetonitrile, filtering, solid use column chromatography to get；The present invention is mainly using solubility as alkalization method in the core methed for isolating and purifying betulin, with other related patents, and ultrasonic wave auxiliary law etc. compares, and experimental implementation is simple, at low cost, and is convenient for industrialized production, and pollutes small；The present invention is applied to betulin preparation field.
Description
Technical field
The present invention relates to betulin preparations.
Background technique
Betulin (Betulin also known as betulinol) is a kind of natural pentacyclic triterpenoid, it is widely present in
In birch-bark.Research shows that betulin has antitumor, antiviral, antiallergy, sterilization, anti-inflammatory, anti-osteoporosis etc. extensive
Bioactivity.But betulin is prepared now, such as alkalization method, there are complicated for operation, at high cost, dirts for ultrasonic wave auxiliary law
Big problem is contaminated, industrialized production is not easy to.
Summary of the invention
The purpose of the present invention is to solve existing betulin extracting methods there are complicated for operation, at high cost, and pollution is big,
The problem of being not easy to industrialized production.And provide a kind of preparation method of betulin.
A kind of preparation method of betulin of the invention, it is comprised the steps of:
One, Japanese birch bark is crushed into powder, is added to refluxing extraction 5-6h in the ethyl alcohol that volumn concentration is 95%, weight
It operates 2 times again；Concentration, products therefrom is betulin crude extract；
Two, by betulin crude extract dichloromethane solution stirring at normal temperature 2-4h, filtering retains filtrate, and by filtrate
It is concentrated to dryness, obtains bright yellow solid；
Three, it by bright yellow solid acetonitrile return stirring 2-6h, filters while hot, retains filter cake to get Off-white solid；
Four, methanol is added in the Off-white solid obtained one step up, and return stirring filters while hot, gives up filter cake, filtrate is cold
But overnight, give up and part is precipitated, be spin-dried for filtrate, obtain solid；
Five, the solid of step 4 is used column chromatography, in petroleum ether: ethyl acetate is to divide under the mobile phase of 1~50:1
From obtaining white solid, as betulin.
The present invention include it is following the utility model has the advantages that
Since the component content in Chinese medicinal material extract is more, and can not be separated by simple method, therefore this
Invention mainly using solubility as the core methed for isolating and purifying betulin, passes through the dissolution to contained substance in Chinese medicine
Property separated, the selected solvent of the present invention is isolated and purified with different substances by many experiments screening, every step, finally
Reach the betulin sample for isolating purity 96% or so.Alkalization method in the method for the present invention and other related patents, ultrasound
Wave auxiliary law etc. compares, and experimental implementation is simple, at low cost, and is convenient for industrialized production, and pollutes small.
The present invention is counted since the betulin crude product extracted, and the finished product for refining final betulin to purifying is always received
Rate is 7.5%~8%.Purity can reach 96% or so.
The present invention removes solvent in acetonitrile hot wash purification step and not can be recycled, other organic solvents used are recyclable sharp again
With, achieve the purpose that recycle emission reduction.The reagent contamination used relative to other methods preparation is smaller, and non-wastewater discharge.Due to
Other organic solvents are recyclable in addition to acetonitrile, therefore lower production costs.
The method production cycle of the invention is relatively short, and betulin crude product is mainly through conventional organic solvent normal-temperature dissolution mistake
Filter；Conventional organic solvent reflux washing, gives up filtrate and retains filter cake；Conventional organic solvent purification；The step point greatly of column chromatography for separation four
From purification process.Easy to operate relative to other methods, actual separation process is more simplified.
Detailed description of the invention
Fig. 1 is that pine gum alcohol project TLC tests contact plate figure under PE:EA=20:1 polarity；
Fig. 2 is that betulin project TLC tests contact plate figure under PE:EA=1:1 polarity；
Fig. 3 is that Yk0010-201803002 crowdes of methanol primary purification HPLC examine spectrogram；
Fig. 4 is betulin process flow chart of the invention.
Specific embodiment
Specific embodiment 1: a kind of preparation method of betulin of present embodiment, it is comprised the steps of:
One, Japanese birch bark is crushed into powder, is added to refluxing extraction 5-6h in the ethyl alcohol that volumn concentration is 95%, weight
It operates 2 times again；Concentration (until being concentrated into the ethanol solution to dripless outflow in system), products therefrom is betulin
Crude extract；
Two, by betulin crude extract dichloromethane solution stirring at normal temperature 2-4h, filtering retains filtrate, and by filtrate
It is concentrated to dryness, obtains bright yellow solid；
Three, it by bright yellow solid acetonitrile return stirring 2-6h, filters while hot, retains filter cake to get Off-white solid；
Four, methanol is added in the Off-white solid obtained one step up, and return stirring filters while hot, gives up filter cake, filtrate is cold
But overnight, give up and part is precipitated, be spin-dried for filtrate, obtain solid；
Five, the solid of step 4 is used column chromatography, in petroleum ether: ethyl acetate is to divide under the mobile phase of 1~50:1
From obtaining white solid, as betulin.
Filtering while hot i.e. acetonitrile solvent in system, which is under reflux state, described in present embodiment filters.
Specific embodiment 2: the present embodiment is different from the first embodiment in that: the solid of step 4 column layer
Analysis separation, in petroleum ether: ethyl acetate is isolated white solid under the mobile phase of 1~30:1.Other and specific implementation
Mode one is identical.
Specific embodiment 3: the present embodiment is different from the first embodiment in that: betulin crude extract and two
The mass volume ratio of chloromethanes solution is 1g:25~35mL.It is other same as the specific embodiment one.
Specific embodiment 4: the present embodiment is different from the first embodiment in that: betulin crude extract and two
The mass volume ratio of chloromethanes solution is 1g:30mL.It is other same as the specific embodiment one.
Specific embodiment 5: the present embodiment is different from the first embodiment in that: bright yellow solid and acetonitrile
Mass volume ratio is 1g:25~35mL.It is other same as the specific embodiment one.
Specific embodiment 6: the present embodiment is different from the first embodiment in that: bright yellow solid and acetonitrile
Mass volume ratio is 1g:28~32mL.It is other same as the specific embodiment one.
Specific embodiment 7: the present embodiment is different from the first embodiment in that: Off-white solid and methanol
Mass volume ratio is 1g:15~25mL.It is other same as the specific embodiment one.
Specific embodiment 8: the present embodiment is different from the first embodiment in that: Off-white solid and methanol
Mass volume ratio is 1g:20mL.It is other same as the specific embodiment one.
The content of present invention is not limited only to the content of the respective embodiments described above, the group of one of them or several specific embodiments
The purpose of invention also may be implemented in contract sample.
Beneficial effects of the present invention are verified by following embodiment:
Embodiment 1
A kind of preparation method of betulin of the present embodiment, it is comprised the steps of:
At powder after Japanese birch bark is crushed, repetitive operation 2 times, dry ethyl alcohol is concentrated in the refluxing extraction 5h in 95% ethyl alcohol
Solvent, resulting product are betulin crude extract, are red brown solid, free from extraneous odour, its yield of repeated experimental verification
Reachable 10% or more.
By betulin crude extract dichloromethane solution cold wash 4h, filtering retains filtrate, and concentrate the filtrate to it is dry,
Bright yellow solid is obtained, free from extraneous odour, its yield of repeated experimental verification reachable 75% or more, product purity can reach 60%
More than.
It by betulin methylene chloride refined products acetonitrile hot wash 6h, filters while hot, it is solid to get milky to retain filter cake
Body, free from extraneous odour, its purity of repeated experimental verification reachable 70% or more, yield is about 40% or more.
Betulin acetonitrile refining product is subjected to refining methanol, i.e. reflux hot wash, then filters while hot, give up filter cake,
After filtrate cool overnight, gives up and part is precipitated, being spin-dried for filtrate can be obtained off-white powder, and product purity can achieve 80%
Left and right, yield are greater than 50%.
Obtained betulin refining methanol product progress TLC is groped to test, is groped under the flow visualizing of PE:EA
Product polarity, and with reference to ultraviolet lamp box as judging basis, experiments verify that learn TLC test in, PE:EA=20:1
Polarity under climb plate and the small impurity of polarity can be separated, and target product stays in origin position, as shown in Figure 1.
Experiments verify that learn TLC experiment in, in the case where EA:PE=1:1, in system target product can climb to
Baseline upper end, and still have a larger polar impurity residual in the position of origin, can be by target product from origin under this polarity condition
Separation, stays in origin position for big polar impurity, as shown in Figure 2.
Separation foundation is tested according to TLC, experiments verify that in normal column chromatography experiment, in the stream of PE:EA=30:1
Under dynamic phase system, target product (verifying through betulin reference substance) can be rushed out, and the betulin product isolated is white
Solid, free from extraneous odour, purity can reach 96% or more, and in short column column chromatography experiment, in the flow visualizing of PE:EA=15:1
Under, target product (verifying through betulin reference substance) can be rushed out, and the betulin product isolated is white solid, nothing
Peculiar smell, purity can reach 91% or more.
Embodiment 2
Betulin parallel laboratory test
The present embodiment is mainly groping for TLC and column chromatography experiment, and the betulin of three batches of parallel laboratory tests preparations is refined
Starting material of the product as TLC experiment and column chromatography experiment, concrete condition are as shown in the table:
The each batch of 1 betulin project crude extract yield of table compares
| Serial number | Sample batch | Crude extract yield | Extract character | Extraction time |
| 1 | Yk0010-201803001 | 20.5g | Brown-red solid | 5h+5h |
| 2 | Yk0010-201803002 | 21g | Brown-red solid | 5h+5h |
| 3 | Yk0010-201803003 | 20.2g | Brown liquid | 5h+5h |
By above-mentioned experiment it is found that mentioning in experiment in betulin Rough Project, yield is in 20g or more (raw material 200), yield
It can reach 10% or more.This step process is easy to operate, but needing to extract twice just can be by the white birch rouge in Japanese birch bark powder
Alcohol component extracts, process stabilizing, and free from extraneous odour generates.
In second step experiment, refined using the method for methylene chloride cold wash, concrete condition is as shown in the table:
The 2 betulin crude extract methylene chloride cold wash table of comparisons of table
| Serial number | Sample batch | Product assay | Product characters | Products weight |
| 1 | Yk0010-201803001 | 63.69% | Bright yellow solid | 15g |
| 2 | Yk0010-201803002 | 67.52% | Bright yellow solid | 15g |
| 3 | Yk0010-201803003 | 65.64% | Bright yellow solid | 16g |
By above-mentioned experiment it is found that yield is in 15 or more (raw materials in the experiment of betulin project methylene chloride cold wash
20g or so), yield can reach 75% or more, and purity is also 60% or more.This step process is easy to operate, without heating,
Technique is highly stable, and free from extraneous odour generates.
In third step experiment, refined using the method for acetonitrile hot wash, concrete condition is as shown in the table:
The 3 betulin methylene chloride refined products acetonitrile hot wash table of comparisons of table
| Serial number | Sample batch | Product assay | Product characters | Products weight |
| 1 | Yk0010-201803001 | 79.41% | Faint yellow solid | 7g |
| 2 | Yk0010-201803002 | 88.18% | Faint yellow solid | 7g |
| 3 | Yk0010-201803003 | 72.74% | Faint yellow solid | 5g |
Above-mentioned experiment is tested it is found that in the experiment of betulin project acetonitrile hot wash since Yk0010-201803003 is criticized
It after acetonitrile hot wash, does not filter while hot, impurity is caused to be precipitated, to carry out secondary refining so yield decline, other two batches
Secondary response Yield comparison is stablized, and for yield 40% or more, purity can achieve 70% or more.
In the experiment of the 4th step, refined using the method for methanol eddy, concrete condition is as shown in the table:
4 betulin acetonitrile refining Methanol product of table recrystallizes the table of comparisons
| Serial number | Sample batch | Product assay | Product characters | Products weight |
| 1 | Yk0010-201803001 | 89.02% | Class yellow powder solid | 4g |
| 2 | Yk0010-201803002 | 78.49% | Faint yellow solid | 4g |
| 3 | Yk0010-201803003 | 72.88% | Faint yellow solid | 2g |
Above-mentioned experiment it is found that in the recrystallization experiment for the first time of betulin project methanol eddy, by filtering while hot and
Cooling crystallization can remove impurity, the difference of product assay mainly since rear two batches solvent peak being distinguished with impurity peaks, from
And lead to the reduction of target product purity, but more acurrate confirmation main peak content, it is specific as shown in Figure 3.And the content of third batch is less
It is few so as to cause yield since two batches are few earlier above for starting material.In conclusion methanol primary purification can be pure by target product
Change to 80% or so, yield is 50% or more.
Embodiment 3
Betulin column chromatography experiment
Since early period also groped many methods to the separation of betulin, wherein also the recrystallization including other reagents is real
It tests, but effect is undesirable, through Literature Consult and previous experiences, the method for the present embodiment proposed adoption TLC is to target product and miscellaneous
The polarity of matter is groped, and concrete condition is as shown in the table:
The table of comparisons is groped in 6 betulin TLC of table experiment
Above-mentioned experiment, can will be small in system under the polarity condition of mobile phase EA:PE=1:20 it is found that in TLC experiment
Polar impurity is separated, and the polarity condition for being then replaced with mobile phase EA:PE=1:1 again can separate target product
Out, the method can be used as the theoretical foundation of the separating experiment of column chromatography, and ratio should be expanded 3 times by practical operation.
Grope after the completion of polarity, also use and scrape wide silica gel plate, and be dissolved out the target product separated with methanol,
After tested, the above-mentioned conclusion groped betulin polarity is demonstrated again.
Grope as a result, using the method for column chromatography to target product polar to target product and impurity is tested by TLC
It is separated, concrete condition is as shown in the table:
The 7 betulin column chromatography experiment table of comparisons one of table
| Serial number | Elute polarity | Target product purity | Product characters | Products weight |
| 1 | EA:PE=1:30 | 96.74% | Off-white powder | Largely |
| 2 | EA:PE=1:3 | 0% | Faint yellow solid | Seldom |
| 3 | EA:PE=1:1 | 20% | Yellow solid | Seldom |
As seen from the above table, the eluent that the experiment of this step is first EA:PE=1:60 with polarity goes out small polar impurity, passes through
To give up after the confirmation of TLC contact plate, then is gone out target product with the eluent of EA:PE=1:30, purity can reach 96.74%, by
In using buttress shaft, loadings are less, and target product is again smaller than 1g.It is verified by the eluent of EA:PE=1:3, no mesh
Mark product is rushed out, thus the mesh that the big polar elution liquid verified above-mentioned polar accuracy, and pass through EA:PE=1:1 is gone out
Marking product is the remaining target product of origin, does not influence experimental result.
8 betulin column chromatography experiment of table compares summary table two
| Serial number | Gradient | Target product purity | Product characters | Products weight |
| 1 | PE:EA=45:1 | 41.15% | Faint yellow solid | On a small quantity |
| 2 | PE:EA=30:1 | 0% | White solid | On a small quantity |
| 3 | PE:EA=15:1 | 91.15% | White solid | Largely |
As seen from the above table, the eluent that the present embodiment is first still EA:PE=1:60 with polarity goes out small polar impurity, warp
Give up after the confirmation of TLC contact plate.Since the present embodiment is separated using short column, 10cm is only loaded, therefore result in EA:PE=
Under the polarity condition of 1:30, eluent does not go out target product, and after increasing polarity, in the polarity condition of PE:EA=15:1
It is lower to be eluted out target product.Purity can reach 91.15%.
In betulin project is respectively tested, it is all made of conventional method and is operated, selected reagent is also routine
Reagent, at present can be by purification of products to 96% or more by last column chromatography experiment, and process stabilizing, it can thus be appreciated that this hair
Bright prepared target product basically reaches testing requirements, subsequent to be confirmed by detection devices such as nuclear-magnetism, mass spectrums.
Claims (8)
1. a kind of preparation method of betulin, it is characterised in that it is comprised the steps of:
One, Japanese birch bark is crushed into powder, is added to refluxing extraction 5-6h in the ethyl alcohol that volumn concentration is 95%, repeat to grasp
Make 2 times；Concentration, products therefrom is betulin crude extract；
Two, by betulin crude extract dichloromethane solution stirring at normal temperature 2-4h, filtering retains filtrate, and filtrate is concentrated
To doing, bright yellow solid is obtained；
Three, it by bright yellow solid acetonitrile return stirring 2-6h, filters while hot, retains filter cake to get Off-white solid；
Four, methanol is added in the Off-white solid obtained one step up, and return stirring filters while hot, gives up filter cake, filtrate is cooled
Night is given up and part is precipitated, is spin-dried for filtrate, obtains solid；
Five, the solid of step 4 is used column chromatography, in petroleum ether: ethyl acetate is to separate under the mobile phase of 1~50:1
To white solid, as betulin.
2. a kind of preparation method of betulin according to claim 1, it is characterised in that by the solid column of step 4
Chromatography, in petroleum ether: ethyl acetate is isolated white solid under the mobile phase of 1~30:1.
3. a kind of preparation method of betulin according to claim 1, it is characterised in that betulin crude extract and two
The mass volume ratio of chloromethanes solution is 1g:25~35mL.
4. a kind of preparation method of betulin according to claim 3, it is characterised in that betulin crude extract and two
The mass volume ratio of chloromethanes solution is 1g:30mL.
5. a kind of preparation method of betulin according to claim 1, it is characterised in that bright yellow solid and acetonitrile
Mass volume ratio is 1g:25~35mL.
6. a kind of preparation method of betulin according to claim 5, it is characterised in that bright yellow solid and acetonitrile
Mass volume ratio is 1g:28~32mL.
7. a kind of preparation method of betulin according to claim 1, it is characterised in that Off-white solid and methanol
Mass volume ratio is 1g:15~25mL.
8. a kind of preparation method of betulin according to claim 7, it is characterised in that Off-white solid and methanol
Mass volume ratio is 1g:20mL.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111233964A (en) * | 2020-03-14 | 2020-06-05 | 哈尔滨源素生物工程有限公司 | Method for extracting and refining betulin and betulinic acid in cortex Betulae Pendulae |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1634972A (en) * | 2004-11-12 | 2005-07-06 | 张梅 | Process for extracting and purifying betulin and betulinic acid |
| CN1810826A (en) * | 2006-02-21 | 2006-08-02 | 东北林业大学 | Betulinol producing process |
| KR100770940B1 (en) * | 2006-05-12 | 2007-10-26 | 에스케이건설 주식회사 | A isolation process for betulin from birch bark |
| CN101200486A (en) * | 2006-12-13 | 2008-06-18 | 上海睿智化学研究有限公司 | Method for abstracting and purifying betulin in birch bark |
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| CN111233964A (en) * | 2020-03-14 | 2020-06-05 | 哈尔滨源素生物工程有限公司 | Method for extracting and refining betulin and betulinic acid in cortex Betulae Pendulae |
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