CN109851480A - A method of high-purity cannabidiol is prepared using dynamic axial compression column - Google Patents
A method of high-purity cannabidiol is prepared using dynamic axial compression column Download PDFInfo
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- CN109851480A CN109851480A CN201910265882.7A CN201910265882A CN109851480A CN 109851480 A CN109851480 A CN 109851480A CN 201910265882 A CN201910265882 A CN 201910265882A CN 109851480 A CN109851480 A CN 109851480A
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Abstract
The present invention provide it is a kind of using dynamic axial compression column preparation high-purity cannabidiol method, comprising: by the Chinese fried dough twist leaf extraction crude product be dissolved in acetonitrile, dilute, filter it is spare；Separation preparation is carried out to filtered crude product using preparative liquid chromatography system, the preparative liquid chromatography system uses dynamic axial compression column, using the mixed solution of acetonitrile and water as mobile phase, by the way of gradient elution and UV detector carries out separation detection, and the fraction of Fractional Collections purpose peak value to sample；The fraction being collected into is subjected to vacuum rotary steam concentration, freeze-drying, obtains white powder product, purity is up to 99.5% or more.The present invention can directly adopt industrial hemp and extract crude product to prepare, pre-treatment is not needed, simply, easy to control, technology simplifies, the mobile phase used is also common reagent in reversed-phase high performance liquid chromatography, suitable for large scale preparation, purity is higher than 99.5%, is fully available for the exploitation of drug and functional food.
Description
Technical field
The present invention relates to industrial abstract technical fields, and in particular to a kind of big using dynamic axial compression column preparation high-purity
The method of numb diphenol.
Background technique
Industrial hemp (Stevia rebaudiana Bertoni) is the annual dioecious draft of Cannabaceae Cannabis
Plant is distributed widely in all over the world.Cannabis plant mainly has wild hemp (Cannabis ruderalis in the world
Janisch), cunjah (Cannabis indica Lam) and cultivation 3 kinds of hemp (Cannabis sativa L), in length
Many Cannabis varieties and subspecies are produced during the biological evolution of phase again.Due to causing the secondary of unreal habituation containing a kind of in hemp
Metabolite-tetrahydrocannabinol (tetrahydrocannabinol, THC), thus become the public known to mother drug plants it
One.In order to facilitate supervision and reasonable employment, the Hemp Varieties definition of THC content < 0.3% in hemp do not had into drugs in the world
The industrial hemp of utility value.At present in the world plant industrial hemp country up to 27, cultivate meet THC content <
0.3% industrial hemp kind 26.Industrial hemp plant is tall and big, and branch is few, and fiber content is high, and economic value is related to making
The many aspects such as paper, weaving, building materials, food, medicine.
Existing research show in industrial hemp non-additive ingredient cannabidiol (cannabidiol, CBD) have it is anti-inflammatory,
It the effects of sterilization, analgesia, antianxiety, antipsychotic, anti-oxidant, improvement learning and memory, neuroprotection and reduction enterocinesia, can use
In the multiple artery sclerosis for the treatment of and Parkinson's disease, prevention myocardial infarction, block Metastasis in Breast Cancer, inhibition neuroglial cytoma
Transfer and inhibition hormone secretion etc., it can also be used to treat glaucoma, the spasticity of paraplegia and multiple sclerosis patient and
The effects of dyskinesia, pain caused by cancer, neuralgia, migraine, epilepsy.Therefore, Devoting Major Efforts To Developing and be a Xiang Liguo using industrial hemp
Favorable to the people and conservation of nature ecological environment green engineering, diversified product have wide international market.Public information at present
In have the reports of some extracting methods about cannabidiol (CBD).For example, CN107344908 A discloses a kind of hemp two
The extracting process and its cannabidiol product of phenol, by throttling expansion separation, are filtered and are disappeared using CO_2 supercritical technology
The subsequent operations such as poison have finally obtained cannabidiol product.CN108083989 A discloses a kind of system of high-purity cannabidiol
Preparation Method is purified using solvent extraction method and macroporous adsorbent resin column chromatography with polyamide column chromatography joint technology, is mixed
Bonding solvent system carries out crystal refining, has finally obtained cannabidiol product.CN104277917 A discloses a kind of rich in hemp
The industrial hemp method of extraction of essential oil and its extract equipment of diphenol, using organic solvent extraction and combine screening washer, fermentation vat,
The equipment such as Rotary Evaporators, ultrasonic agitation tank, disk centrifugal separator, pressurization chromatographic silica gel post gradually sieve industrial hemp
The operating procedures such as choosing, baking, extraction, reprocessing, filtering, monitoring, loading, chromatography, concentration and finished product, it is final to propose to be rich in hemp
The industrial hemp essential oil of diphenol.
Currently, research report relevant for the extracting process of the medicinal ingredient cannabidiol of industrial hemp is more, mostly
To be isolated and purified using macroporous adsorbent resin column chromatography or polyamide column chromatography joint technology, this separation and extraction technology
Yield is low, it is not high to extract CBD purity.
Summary of the invention
The purpose of the present invention is to provide a kind of sides using dynamic axial compression column preparation high-purity cannabidiol (CBD)
Method, technical thought are the principles according to reversed-phased high performace liquid chromatographic, are prepared using dynamic axial compression column large-scale separation
Cannabidiol solves time length and the not high technical problem of purity existing during purifying cannabidiol at present, behaviour
To make simply, product content is high, favorable repeatability, method includes the following steps:
(1) industrial hemp floral leaf extraction crude product is dissolved in water or acetonitrile, generally matches industrial hemp floral leaf extraction crude product
It is made the saturated solution for being dissolved in water-acetonitrile, when specific implementation can be adjusted according to practical solute effect, and saturated solution is filtered
It is spare；Industrial hemp floral leaf is Chinese fried dough twist leaf, and extracting crude product is the gained after organic solvent deposit, wherein cannabidiol content
For 30-40%.
(2) prepared solution is taken, is separated with the dynamic axial compression column of populated fixed phase stuffing, dynamic is passed through
Axial compression column, mobile phase are the mixed solution of acetonitrile and water, are separated through gradient elution, are carried out using UV detector to sample
Detection, Fractional Collections cannabidiol correspond to the fraction of bands of a spectrum；The fixed phase stuffing is the anti-of octadecylsilane chemically bonded silica
Phase silica gel, particle size range are 10 μm -75 μm, and the filling inside diameter ranges of the dynamic axial compression column are 500-1500mm, are had
Effect column length is 500-1500mm.The volume ratio of acetonitrile and water is 20:80-40:60 in the mobile phase.
(3) solvent in the correspondence bands of a spectrum fraction collected in step (2) is evaporated, it is 99.5% or more that content, which can be obtained,
Cannabidiol monomer.
Dynamic axial compression column is a kind of technology that good separation effect can be kept in column chromatography, and preparation chromatography neck
The optimal column packing technique in domain has from luggage column, maintains column pressure, voluntarily unloads column, have concurrently chromatographic column and packing column machine function and
The requirement such as continuity, uniformity, stability and compactness.
Beneficial effects of the present invention are not only in that the dress column time is short, and column effect is high, and without dead volume, higher column effect allows separation
Purification process is effectively, primary to collect the requirement and purpose that can reach preparation；And it directlys adopt and slightly mentions industrial hemp
Crude product is extracted to prepare, does not need a large amount of pre-treatment, simple, easy to control, technology simplifies, and the mobile phase used is also anti-
Common reagent in phase high performance liquid chromatography is suitable for large scale preparation.In high performance liquid chromatography measurement, purity is higher than
99.5%, it is fully available for the exploitation of drug and functional food.
Detailed description of the invention
The chromatogram of Figure 1A and Figure 1B industrial hemp crude product；
The CBD chromatogram (cannabidiol that 145min-240min is pre-collecting) of Fig. 2 preparing chromatograph in industry；
The chromatogram of Fig. 3 A and Fig. 3 B cannabidiol finished product.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention,
Technical solution of the present invention is clearly and completely described, it is clear that described embodiment is that a part of the invention is implemented
Example, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making creativeness
Every other embodiment obtained, shall fall within the protection scope of the present invention under the premise of labour.
Embodiment 1
It is including following several the present embodiment provides a kind of method using dynamic axial compression column preparation high-purity cannabidiol
A step:
(1) 1g industrial hemp floral leaf crude product (CBD content is 30.2%, and chromatogram is as shown in FIG. 1A and 1B) is taken to be dissolved in
Water is configured to saturated solution, and ultrasonic treatment is filtered to remove solid particle, and it is stand-by to collect filtrate.
(2) filtrate is pumped into dynamic axial compression column preparing chromatography system, column is filled having a size of 800 × 1000mm of Φ, filled out
Material is the reverse phase silica gel of octadecylsilane chemically bonded silica, and partial size 10um, applied sample amount 1g, 0-40 minute, mobile phase is acetonitrile
With the mixed solution of water, by 20:80 to 40:60, the Detection wavelength of UV, visible light luminosity detector is the volume ratio of acetonitrile/water
220nm collects retention time in the fraction of 145-240min cannabidiol, as shown in Fig. 2, after cannabidiol elution,
Mobile phase switches to 100% acetonitrile, and rear end impurity is gone out, and a separation cycle terminates.
(3) after the fraction being collected into being carried out vacuum rotary steam concentration, freeze-drying, HPLC tests and analyzes such as Fig. 3 A and Fig. 3 B
Shown, cannabidiol purity is respectively 99.3%.
Embodiment 2
It is including following several the present embodiment provides a kind of method using dynamic axial compression column preparation high-purity cannabidiol
A step:
(1) it takes 1g industrial hemp floral leaf crude product (CBD content be 33.9%) to be dissolved in water, is configured to saturated solution, at ultrasound
Reason is filtered to remove solid particle, and it is stand-by to collect filtrate.
(2) filtrate is pumped into dynamic axial compression column preparing chromatography system, column is filled having a size of 800 × 1000mm of Φ, filled out
Material is the reverse phase silica gel of octadecylsilane chemically bonded silica, and partial size 10um, applied sample amount 1g, 0-45 minute, mobile phase is acetonitrile
With the mixed solution of water, by 40:80 to 40:60, the Detection wavelength of UV, visible light luminosity detector is the volume ratio of acetonitrile/water
220nm collects retention time in the fraction of 155-240min cannabidiol, after cannabidiol elution, mobile phase switching
At 100% acetonitrile, rear end impurity is gone out, a separation cycle terminates.
(3) after the fraction being collected into being carried out vacuum rotary steam concentration, freeze-drying, HPLC is tested and analyzed, and cannabidiol is pure
Degree is respectively 99.5%.
Embodiment 3
It is including following several the present embodiment provides a kind of method using dynamic axial compression column preparation high-purity cannabidiol
A step:
(1) it takes 1g industrial hemp floral leaf crude product (CBD content be 35.6%) to be dissolved in water, is configured to saturated solution, at ultrasound
Reason is filtered to remove solid particle, and it is stand-by to collect filtrate.
(2) filtrate of step 1 being pumped into dynamic axial compression column preparing chromatography system, column fills having a size of Φ 800 ×
1000mm, filler are the reverse phase silica gel of octadecylsilane chemically bonded silica, partial size 10um, applied sample amount 1g, 0-40 minute, flowing
It is mutually the mixed solution of acetonitrile and water, the volume ratio of acetonitrile/water is by 20:80 to 40:60, the detection of UV, visible light luminosity detector
Wavelength is 220nm, collects retention time in the fraction of 155-220min cannabidiol, after cannabidiol elution, flowing
100% acetonitrile is mutually switched to, rear end impurity is gone out, a separation cycle terminates.
(3) after the fraction being collected into being carried out vacuum rotary steam concentration, freeze-drying, HPLC is tested and analyzed, and cannabidiol is pure
Degree is respectively 99.6%.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art within the technical scope of the present disclosure, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (5)
1. a kind of method using dynamic axial compression column preparation high-purity cannabidiol, which comprises the following steps:
(1) by the Chinese fried dough twist leaf extraction crude product be dissolved in water or acetonitrile, dilute, filter it is spare；
(2) separation preparation is carried out to filtered crude product using preparative liquid chromatography system: by dynamic axial compression column, flowing
It is mutually the mixed solution of acetonitrile and water, gradient elution separates, and UV detector detects sample, Fractional Collections purpose peak value
Fraction；
(3) fraction being collected into is subjected to vacuum rotary steam concentration, freeze-drying, obtaining white powder is cannabidiol.
2. the method according to claim 1 using dynamic axial compression column preparation high-purity cannabidiol, feature exist
In: it is the gained after organic solvent deposit that the Chinese fried dough twist leaf, which extracts crude product, and wherein cannabidiol content is 30-40%.
3. the method according to claim 1 using dynamic axial compression column preparation high-purity cannabidiol, feature exist
In: filling fixed phase stuffing is the anti-of octadecylsilane chemically bonded silica in the dynamic axial compression column of the liquid chromatographic system
Phase silica gel, particle size range are 10 μm -75 μm.
4. the method according to claim 1 using dynamic axial compression column preparation high-purity cannabidiol, feature exist
In: the filling inside diameter ranges of the dynamic axial compression column are 500-1500mm, effective column length 500-1500mm.
5. the method according to claim 1 using dynamic axial compression column preparation high-purity cannabidiol, feature exist
In: the volume ratio of acetonitrile and water is 20:80-40:60 in the mobile phase.
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| CN110283048A (en) * | 2019-06-28 | 2019-09-27 | 云南翰谷生物科技有限公司 | The preparation method of cannabidiol crystal |
| CN111039761A (en) * | 2019-12-31 | 2020-04-21 | 江苏汉邦科技有限公司 | Method for purifying cannabidiol |
| CN112979488A (en) * | 2021-04-02 | 2021-06-18 | 黑龙江展延自动化科技有限公司 | Cannabinoid production method based on axial dynamic extraction two-fluid separation technology |
| CN115724724A (en) * | 2022-11-23 | 2023-03-03 | 黑龙江省科学院大庆分院 | Method for preparing high-purity cannabidiol by dynamic axial compression column purification system eluent crystallization |
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| CN110283048A (en) * | 2019-06-28 | 2019-09-27 | 云南翰谷生物科技有限公司 | The preparation method of cannabidiol crystal |
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| CN115724724A (en) * | 2022-11-23 | 2023-03-03 | 黑龙江省科学院大庆分院 | Method for preparing high-purity cannabidiol by dynamic axial compression column purification system eluent crystallization |
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