CN109568389A - A kind of preparation method of high-purity cannabinoids extract - Google Patents
A kind of preparation method of high-purity cannabinoids extract Download PDFInfo
- Publication number
- CN109568389A CN109568389A CN201710908169.0A CN201710908169A CN109568389A CN 109568389 A CN109568389 A CN 109568389A CN 201710908169 A CN201710908169 A CN 201710908169A CN 109568389 A CN109568389 A CN 109568389A
- Authority
- CN
- China
- Prior art keywords
- extract
- preparation
- solvent
- cannabinoids
- thick paste
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/60—Moraceae (Mulberry family), e.g. breadfruit or fig
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/17—Preparation or pretreatment of starting material involving drying, e.g. sun-drying or wilting
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/35—Extraction with lipophilic solvents, e.g. Hexane or petrol ether
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
The invention discloses a kind of preparation methods of cannabinoids extract, this method comprises: the extract part of hemp is crushed, baking obtains medicinal powder；By medicinal powder solvent extraction, extracting solution is obtained, is concentrated, obtains thick paste；By thick paste solvent extraction, upper liquid is taken, is concentrated, obtains thick paste；Thick paste pH is adjusted to alkalinity, is filtered, gained filtrate adjusts pH to acidity, and filtering obtains sediment；Sediment is dissolved with solvent, acquired solution carries out column chromatography, elution；Eluent is concentrated, cannabinoids extract is obtained.In the method, raw materials used, reagent and instrument are cheap and easy to get, and cost is relatively low；And the extract of high quality can be obtained, the cannabinol compounds compared with multiple types are remained, the wasting of resources is avoided, wherein the total content of cannabinol compounds reaches 80% or more, and especially THC content is 1 ‰ hereinafter, Product Safety is higher；And it is preferable respectively to prepare lot stability, it is easy to accomplish industrialization.
Description
Technical field
The present invention relates to technical field of chemistry, and in particular to a kind of preparation method of high-purity cannabinoids extract.
Background technique
Hemp (scientific name: Cannabis sativa L.) Cannabaceae, Cannabis plant, You Mingma, Chinese fiber crops, fire fiber crops, mountain silk
Seedling, jute have important agricultural and medical value.It can be made one in hemp containing a kind of toxic component THC (tetrahydrocannabinol)
Unreal habituation is caused, drugs can be made, was once forbidden cultivating within suitable long-term.
Since the economy of hemp, medical value are high, the raw material hemp for specializing in industrial use is referred to as " industrial hemp ",
Tetrahydrocannabinol (THC) content in growth period hemp floral leaf does not have less than 3/1000ths and extracts toxic component tetrahydro hemp
The value of phenol is sucked directly as drugs, can legal progress large-scale planting and industrialized developing utilization.
Currently, people have isolated more than 500 substances from hemp plant, wherein cannabinol compounds at least 86
Kind, cannabinol compounds are a kind of terpenes phenolic compounds, and research confirms, containing there are many cannabinoids in industrial hemp plant
Compound, wherein main phenolic compound has cannabidiol (CBD), cannabidivarin (CBDV), cannabinol (CBN), hemp
Terpene phenol (CBG), cannabichromene (CBC), tetrahydrocannabinol (THC) etc. more than 80.These phenolic substancess have been shown to have
Very strong pharmacological activity, e.g., CBD do not have neurotoxicity, can hinder influence of the THC to nerve system of human body, and have bright
The pharmacological activity such as aobvious anti-spasm, resisting rheumatoid arthritis, antianxiety have huge industry development value；CBD and THCV can shadow
Lipid and glycometabolism are rung, is likely to become new selection of control type 2 diabetic patient's blood glucose etc., CBDV is living with preferable anti-epileptic
Property, while some researches show that CBDV can reduce nausea, help to treat gastrointestinal problems, and the joint of these phenolic substancess
It is stronger using acting on.But the THC in hemp, which has, causes addiction hallucinogenic action, using industrial hemp as raw material, obtains mentioning without THC
Object is taken, it is necessary to provide high active substance raw material for pharmaceutical preparation.
With cannabinoids hemp Polyphenols extract as main component, because its structure is similar, the removal difficulty of THC compared with
Greatly, research is less, and patent application CN106860492A discloses a kind of preparation method of cannabinol compounds, but method walks
Rapid complexity, yield are low, and THC is not used as harmful substance to remove, and are not suitable for practical application；Patent application CN106278828A is public
A kind of method that CBD is extracted from industrial hemp floral leaf is opened, CBD purity is higher in finished product, and eliminates THC, but in extraction
Other cannabinol compounds, such as CBDV, THCV are not accounted for, resource has certain waste, and extracting method step is more
It is cumbersome, it is unfavorable for industrialized production.
Summary of the invention
In order to overcome the deficiencies of the prior art, the present invention is intended to provide a kind of preparation process of high-purity cannabinoids extract,
Wherein the total content of cannabinol compounds reaches 80% or more in the extract, and each main active and its content are distinguished
Are as follows: CBDV, 10%-13%；CBD, 55%-60%；CBG, 4%-5%；THCV, 4%-5%；THC, content a ten thousandth with
Under.
First aspect present invention provides the preparation method of high-purity cannabinoids extract.
Second aspect of the present invention provides a kind of high-purity cannabinoids extract of above method preparation.
Third aspect present invention provides a kind of application of above-mentioned cannabinoids extract in medicine preparation.
Specifically, the preparation method of cannabinoids extract provided by the invention includes the following steps:
(1) extract part of hemp crushes, and baking obtains medicinal powder；
(2) by medicinal powder solvent extraction obtained by step (1), extracting solution is obtained, the extracting solution is concentrated, is obtained thick
Cream；
(3) by thick paste solvent extraction obtained by step (2), upper liquid is taken, the upper liquid is concentrated, thick paste is obtained；
(4) thick paste obtained by step (3) is adjusted into pH to alkalinity, filtered, gained filtrate adjusts pH to acidity, and filtering obtains
Sediment；
(5) step (4) gained sediment is dissolved with solvent, acquired solution carries out column chromatography, elution；
(6) eluent obtained by step (5) is concentrated, obtains cannabinoids extract.
Preferably, extract part described in step (1) is selected from: marihuana, cannabis, cannabis root, hemp stalk core and big
The combination of one or more of numb seed dregs of rice arbitrary proportion；It is furthermore preferred that the extract part is for cannabis and/or greatly
Sesame slices, it is further preferred that the cannabis and/or marihuana use the cannabis and/or marihuana of full-bloom stage.
Preferably, hemp described in step (1) be selected from one of industrial hemp, osculant hemp or medicinal hemp or
Two or more combinations；More preferably industrial hemp.
Preferably, hemp extract part described in step (1) is (such as to dry, dry by preliminarily dried after picking
Drying mode) hemp extract part, it is furthermore preferred that the hemp extract part moisture content is 10-15%, dirt content exists
3% or less.
It is cannabinoids that baking described in step (1), which is conducive to some other conversions in hemp extract part,
Object is closed, becomes cannabinol (CBN) as cannabinol can remove converting carboxylate groups by non-enzymatic reaction, phenolic compound is total after baking
Content can be improved 50% or more；Preferably, the temperature of the baking is 100-150 DEG C (specific such as 100,110,120,130,140
Or 150 DEG C), and/or, the time of baking is 20-80min (specific such as 20,40,60 or 80min).Preferably, institute in step (1)
The crushing stated is that hemp extract part is crushed to 10-80 mesh (specific such as 10,20,30,40,50,60,70 or 80 mesh).
Preferably, in medicinal powder described in step (1) moisture content less than 6%.
Preferably, solvent described in step (2) is ethyl alcohol, it is furthermore preferred that it is 60-95% (v/ that the ethyl alcohol, which is concentration,
V, it is specific such as 60%, 70%, 80%, 90% or ethyl alcohol 95%).
Preferably, solvent usage described in step (2) is that 5-15 times of medicinal material amount is (specific such as 5,8,10,12 or 15 times of medicines
Material amount).
Preferably, extraction time described in step (2) is 1-5 times (specific such as 1,2,3,4 or 5 time), each extraction time
For 1-3h.
Preferably, extracting method described in step (2) is selected from: cold-maceration, ultrasonic extraction, reflux extraction and leaching are filtered
The combination of one or more of method；It is furthermore preferred that extracting method described in step (2) is cold-maceration.
Preferably, the cold-maceration extraction conditions are as follows: extracting 1-5 with 5-15 times of medicinal material amount 60-95% ethyl alcohol cold soaking
It is secondary, each 1-3h.
The extraction of step (3) is deimpurity committed step, impurity can be removed 70% or more.
Preferably, extractant described in step (3) is selected from: ethyl acetate, n-butanol, n-hexane, petroleum ether and two
The combination of one or more of chloromethanes；It is furthermore preferred that extractant described in step (3) is n-hexane.
Preferably, extractant dosage described in step (3) is that 1-6 times of medicinal material amount is (specific such as 1,2,3,4,5 or 6 times
Medicinal material amount).
Preferably, extraction times described in step (3) are 1-3 times (specific such as 1,2 or 3 time).
Preferably, thickening temperature described in step (2) and/or (3) is 50-70 DEG C, more preferably 65 DEG C.
Preferably, thick paste relative density described in step (2) and/or (3) is 1.05-1.35 (measuring at 50 DEG C) (tool
Body such as 1.05,1.08,1.10,1.20,1.30 or 1.35).
The phenolic compound in thick paste obtained by step (3) can be further purified in adjusting pH described in step (4), be such as adjusted to
Alkalinity can make phenolic compound at salt, and after filtering, adjusting filtrate pH to acidity can convert above-mentioned salt to corresponding phenols chemical combination
Object.
Preferably, adjusting pH described in step (4) includes the steps that highly basic, which is added, adjusts pH to alkalinity；It is furthermore preferred that
The highly basic is selected from: the combination of one or more of calcium hydroxide, barium hydroxide, potassium hydroxide and sodium hydroxide,
In one embodiment of the present of invention, the highly basic is sodium hydroxide.
Preferably, the alkaline pH in step (4) is pH10.0-12.0, more preferably pH11.0.
Preferably, adjusting pH described in step (4) includes the steps that weak acid for adjusting pH is added to acidity；It is furthermore preferred that
The weak acid is selected from: the combination of one or more of acetic acid, sulfurous acid and phosphoric acid, in one embodiment of the present of invention
In, the weak acid is acetic acid.
Preferably, the acid pH in step (4) is pH4.0-5.0, more preferably pH4.6.
Preferably, step (4) further includes whipping step after adjusting pH to alkalinity, it is furthermore preferred that mixing time is 0.5-
2h。
Preferably, solvent described in step (5) is selected from: ethyl acetate, n-butanol, n-hexane, petroleum ether and dichloromethane
The combination of one or more of alkane.
Preferably, solvent usage described in step (5) is 0.5-2 times of (specific such as 0.5,1,1.5 or 2 times of medicinal material amount) medicine
Material amount.
Preferably, the chromatography of column described in step (5) chromatography column packing used is silica filler, it is furthermore preferred that described
Silica filler is selected from: amorphous silica gel, spherical silica gel and silica white.
Preferably, type of elution described in step (5) is to carry out gradient elution to chromatographic column using eluting solvent；It is more excellent
Choosing, the elution step includes: first then to obtain target product portion with the elution of eluting solvent 2 with the elution removal of impurities of eluting solvent 1
Divide (cannabinol compounds adsorbed in chromatographic column).
Preferably, the eluting solvent is selected from: acetone-petroleum ether mixed liquor, methylene chloride-n-hexane mixed liquor, acetic acid
Ethyl ester-heptane mixture and dichloromethane-petroleum ether mixed liquor.
Preferably, the eluting solvent 1 is selected from: acetone-petroleum ether mixed liquor that volume ratio is 1:1, volume ratio 1:9
Methylene chloride-n-hexane mixed liquor and volume ratio be one of 1:30 ethyl acetate-heptane mixed liquor.
Preferably, the dosage of the eluting solvent 1 is 2-8 times of (specific such as 2,3,4,5,6,7 or 8 times) column volume, more
Preferably 4-6 times of column volume.
Preferably, the eluting solvent 2 is selected from: acetone-petroleum ether mixed liquor that volume ratio is 7:3, volume ratio 2:8
Methylene chloride-n-hexane mixed liquor and volume ratio be one of 1:25 ethyl acetate-heptane mixed liquor.
Preferably, the dosage of the eluting solvent 2 is 2-8 times of (specific such as 2,3,4,5,6,7 or 8 times) column volume, more
Preferably 5-7 times of column volume.
Preferably, gradient elution described in step (5) further includes after elution removal of impurities and elution obtain target product part
The step of eluting THC with eluting solvent 3；It is furthermore preferred that gained eluent is destroyed, concentrated acid (such as concentrated hydrochloric acid, concentrated nitric acid are such as used
Deng) destroy.
Preferably, the eluting solvent 3 is selected from: acetone-petroleum ether mixed liquor that volume ratio is 8:2, volume ratio are 4:6's
One of the ethyl acetate-heptane mixed liquor that acetone-petroleum ether mixed liquor and volume ratio are 1:10.
Preferably, the dosage of the eluting solvent 2 is 2-8 times of (specific such as 2,3,4,5,6,7 or 8 times) column volume, more
Preferably 4-6 times of column volume.
Preferably, concentration described in step (6) is to be concentrated under reduced pressure；It is furthermore preferred that the temperature being concentrated under reduced pressure is 55-70
DEG C, and/or, pressure is -0.10MPa.
Specifically, in cannabinoids extract provided by the invention, cannabinol compounds total content is greater than 80%.
Preferably, THC content exists in the cannabinoids extractBelow.
Preferably, one of CBD, CBDV, CBG and THCV or a variety of are included in the cannabinoids extract；More
It preferably, include CBD, CBDV, CBG and THCV in the cannabinoids extract；It is further preferred that the cannabinoids mention
Taking CBD content in object is 55-60%, and CBDV content is 10-13%, and CBG content is 4-5%, and THCV content is 4-5%.
Specifically, in the application of above-mentioned cannabinoids extract provided by the invention in medicine preparation, the drug is
The drug for treating epilepsy.
Cannabinoids extract of the present invention, which is alternatively arranged as further isolating and purifying, obtains each cannabinoids chemical combination
The raw material of object single-item.
The preparation method of cannabinoids extract provided by the invention, raw material used, reagent and instrument are cheap and easy to get, at
This is lower, and the operation of use and method simply easily carry out；And high quality hemp Polyphenols extract can be obtained, it remains more
The cannabinol compounds of type, such as CBD, CBDV, CBG and THCV, avoid the wasting of resources, wherein cannabinoids chemical combination
The total content of object reaches 80% or more, and Psychotoxicity ingredient THC content existsHereinafter, ensureing Product Safety；
And it is higher respectively to prepare lot stability, constituent content and activity are relatively stable in product, it is easy to accomplish industrialization.
Detailed description of the invention
Fig. 1 show the extraction analyte detection HPLC chromatogram of the preparation of the embodiment of the present invention 1.
Fig. 2 show the extraction analyte detection HPLC chromatogram of the preparation of the embodiment of the present invention 2.
Fig. 3 show the extraction analyte detection HPLC chromatogram of the preparation of the embodiment of the present invention 3.
Specific embodiment
Unless otherwise defined, all technical and scientific terms used herein have with the present invention relates to the technologies in field
The normally understood identical meaning of personnel, the following abbreviation such as occurred in the present invention and its corresponding substance are as follows:
Heretofore described " cannabinoids extract " refers to the original from hemp extract part (such as cannabis and/or leaf)
The product extracted in material can be liquid or solid form, wherein comprising at least one cannabinol compounds, preferably
, CBD, CBDV, CBG and THCV are included at least in " cannabinoids extract " of the invention, and THC content existsHereinafter,
Particularly, in the extract product prepared by the embodiment of the present invention, THC is not detected.
Unless stated otherwise, heretofore described " content " is generally mass content, and CBDV's contains such as in extract
Amount is 10%-13%, and refer to: in extract, the quality of CBDV accounts for the 10%-13% of extract gross mass.
The description such as heretofore described " x times of crude drug amount ", " x times of medicinal material amount ", refers to the solvent such as n-hexane, stone of use
The volume of oily ether etc. is x times of quality of medicinal material, specifically, such as " 1 times of medicinal material amount ", if quality of medicinal material is 1g, the use of solvent for use
Amount is 1ml.
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 institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, originally
Field those of ordinary skill every other embodiment obtained without creative efforts, belongs to the present invention
The range of protection.
Hemp extract part raw material used in the embodiment of the present invention are as follows: floral leaf raw material is the mature hemp floral leaf of the 7-9 month,
It dries in the shade, is THC content in 0.3% industrial hemp below.Unless stated otherwise, other reagents are commercial products.
Embodiment 1
Experimental procedure is as follows:
(1) crushing industrial hemp floral leaf raw material is 60 mesh coarse powder, at 150 DEG C, toasts 80min, moisture 2.2%；
(2) medicinal material for obtaining step (1) is extracted using cold-maceration, with 15 times of 95% ethyl alcohol soaking at room temperature 3h, extracts 5
It is secondary, merge to obtain extracting solution；
(3) by step (2) obtains 65 DEG C of extracting solution be concentrated into thick paste (measuring at 1.08,50 DEG C of relative density)；
(4) thick paste dosing material 6 times of the amount n-hexane extraction 3 times for obtaining step (3) stirs 1h, upper layer is taken after being layered,
Merge upper liquid, 65 DEG C are concentrated into thick paste (measuring at 1.08,50 DEG C of relative density)；
(5) thick paste obtained to step (4) is added sodium hydroxide and adjusts pH to 11, and 1h is sufficiently stirred, and filters, and filtrate adds again
Enter second acid for adjusting pH to 4.6, filtering obtains insoluble sediment；
(6) petroleum ether dissolution for the 1 times of crude drug amount of insoluble sediment for obtaining step (5), excessively silica gel column chromatography, third
Ketone: petroleum ether (volume ratio: 1:1, the volume ratio that the ratio of component both is respectively in following eluent) 5 times of cylinders of elution
Product is impurity part, recycling design；Acetone: petroleum ether (7:3) elutes 6 times of column volumes, collects second part eluent, concentration
It is afterwards active component extract；Acetone: petroleum ether (8:2) 5 times of column volumes of elution are the part based on tetrahydrocannabinol, through dense
Enriching hydrochloric acid is destroyed after contracting；
(7) the second part eluent for obtaining step (6) is concentrated under reduced pressure, 55-70 DEG C, -0.10MPa, until stiff paste,
Up to cannabinoids extract, the content of the ingredients such as CBDV, CBD, CBG, THCV and THC in the analysis detection extract.
Sample detection analysis method is as follows:
Chromatographic condition and system suitability: using octadecylsilane chemically bonded silica as filler；It is flowing with acetonitrile
Phase A carries out isocratic elution by A (%): B (%)=80:20 using water as Mobile phase B；Detection wavelength is 210nm.Number of theoretical plate is pressed
The peak CBD, which calculates, should be not less than 2500.
The preparation of reference substance solution: precision weighs CBD reference substance, and adding methanol that every 1ml is made, respectively the reference substance containing 0.1mg is molten
Liquid to get；Precision weighs CBDV reference substance, add methanol be made every 1ml respectively the reference substance solution containing 0.05mg to get；Precision claims
Take THCV reference substance, add methanol be made every 1ml respectively the reference substance solution containing 0.01mg to get；Precision weighs CBG reference substance, adds
Methanol be made every 1ml respectively the reference substance solution containing 0.01mg to get；Precision weighs tetrahydrocannabinol reference substance, and methanol is added to be made
Every 1ml respectively the reference substance solution containing 0.01mg to get.
The preparation of test solution: taking finished product 5mg, adds methanol constant volume to 50ml, is filtered, taken with (0.45 μm) of miillpore filter
Subsequent filtrate to get.
Measuring method: accurate absorption reference substance solution and each 10 μ l of test solution respectively, injection liquid chromatograph, measurement,
To obtain the final product.
The detection chromatogram of extract is as shown in Figure 1, wherein retention time and corresponding substance are as follows: 4.728 are
CBDV, 7.466 be CBG, and 7.921 be CBD, and 8.772 be THCV.
As a result: in the extract that the present embodiment is prepared, cannabinoids substance total content be 84%, each chief active at
Point and its content be respectively as follows: CBDV, 11%；CBD, 58%；CBG, 4.3%；THCV, 4.1%；THC is not detected.
Embodiment 2
Experimental procedure is as follows:
(1) crushing industrial hemp floral leaf raw material is 60 mesh coarse powder, at 100 DEG C, toasts 20min, moisture 5.1%；
(2) medicinal material for obtaining step (1) is extracted using cold-maceration, with 5 times of 60% ethyl alcohol soaking at room temperature 1h, is extracted 1 time；
(3) by step (2) obtains 65 DEG C of extracting solution be concentrated into thick paste (measuring at 1.08,50 DEG C of relative density)；
(4) thick paste dosing material 1 times of the amount n-hexane extraction 1 time for obtaining step (3) stirs 1h, upper layer is taken after being layered,
65 DEG C are concentrated into thick paste (measuring at 1.08,50 DEG C of relative density)；
(5) thick paste obtained to step (4) is added sodium hydroxide and adjusts pH to 11, and 1h is sufficiently stirred, and filters, and filtrate adds again
Enter second acid for adjusting pH to 4.6, filtering obtains insoluble sediment；
(6) methylene chloride of 1 times of crude drug amount of the insoluble sediment for obtaining step (5) dissolves, excessively silica gel column chromatography, and two
Chloromethanes: n-hexane (1:9) elutes 5 times of column volumes, is impurity part, recycling design；Methylene chloride: n-hexane (2:8) elution 6
Times column volume collects second part eluent, is active component extract after concentration；Acetone: petroleum ether (4:6) elutes 5 times
Column volume is the part based on tetrahydrocannabinol, and concentrated rear enriching hydrochloric acid is destroyed；
(7) the second part eluent for obtaining step (6) is concentrated under reduced pressure, 55-70 DEG C, -0.10MPa, until stiff paste,
Up to cannabinoids extract, the content of the ingredients such as CBDV, CBD, CBG, THCV and THC, analysis in the analysis detection extract
Detection method is referring to embodiment 1.
The detection chromatogram of extract is as shown in Figure 2, wherein retention time and corresponding substance are as follows: 4.726 are
CBDV, 7.455 be CBG, and 7.907 be CBD, and 8.769 be THCV.
As a result: in the extract that the present embodiment is prepared, cannabinoids substance total content be 84%, each chief active at
Point and its content be respectively as follows: CBDV, 11%；CBD, 56%；CBG, 4.2%；THCV, 4.3%；THC is not detected.
Embodiment 3
Experimental procedure is as follows:
(1) crushing industrial hemp floral leaf raw material is 60 mesh coarse powder, at 120 DEG C, toasts 40min, moisture 3.3%；
(2) medicinal material for obtaining step (1) is extracted using cold-maceration, with 10 times of 80% ethyl alcohol soaking at room temperature 2h, extracts 2
It is secondary, merge to obtain extracting solution；
(3) by step (2) obtains 65 DEG C of extracting solution be concentrated into thick paste (measuring at 1.08,50 DEG C of relative density)；
(4) the 2 times of n-hexane extractions of thick paste dosing material amount for obtaining step (3) twice, stir 2h, take after being layered
Layer merges upper liquid, and 65 DEG C are concentrated into thick paste (measuring at 1.08,50 DEG C of relative density)；
(5) calcium hydroxide is added in the thick paste obtained to step (4) and adjusts pH to 11,1h is sufficiently stirred, filter, filtrate is again
Second acid for adjusting pH is added to 4.6, filtering obtains insoluble sediment；
(6) ethyl acetate of 1 times of crude drug amount of the insoluble sediment for obtaining step (5) dissolves, and crosses silica gel column chromatography, second
Acetoacetic ester: heptane (1:30) elutes 5 times of column volumes, is impurity part, recycling design；Ethyl acetate: heptane (1:25) elutes 6 times
Column volume collects second part eluent, is active component extract after concentration；Ethyl acetate: heptane (1:10) elutes 5 times
Column volume is the part based on tetrahydrocannabinol, and concentrated rear enriching hydrochloric acid is destroyed；
(7) the second part eluent for obtaining step (6) is concentrated under reduced pressure, 55-70 DEG C, -0.10MPa, until stiff paste,
Up to cannabinoids extract, the content of the ingredients such as CBDV, CBD, CBG, THCV and THC, analysis in the analysis detection extract
Detection method is referring to embodiment 1.
The detection chromatogram of extract is as shown in Figure 3, wherein retention time and corresponding substance are as follows: 4.724 are
CBDV, 7.452 be CBG, and 7.907 be CBD, and 8.757 be THCV.
As a result: in the extract that the present embodiment is prepared, cannabinoids substance total content be 84%, each chief active at
Point and its content be respectively as follows: CBDV, 13%；CBD, 55%；CBG, 4.6%；THCV, 4.4%；THC is not detected.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, made any modification, equivalent replacement etc. be should all be included in the protection scope of the present invention.
Claims (14)
1. a kind of preparation method of cannabinoids extract, includes the following steps:
(1) extract part of hemp crushes, and baking obtains medicinal powder；
(2) by medicinal powder solvent extraction obtained by step (1), extracting solution is obtained, the extracting solution is concentrated, thick paste is obtained；
(3) by thick paste solvent extraction obtained by step (2), upper liquid is taken, the upper liquid is concentrated, thick paste is obtained；
(4) thick paste obtained by step (3) is adjusted into pH to alkalinity, filtered, gained filtrate adjusts pH to acidity, and filtering is precipitated
Object；
(5) step (4) gained sediment is dissolved with solvent, acquired solution carries out column chromatography, elution；
(6) eluent obtained by step (5) is concentrated, obtains cannabinoids extract.
2. preparation method as described in claim 1, which is characterized in that extract part described in step (1) is selected from: hemp
The combination of one or more of leaf, cannabis, cannabis root, hemp stalk core and hemp seed meal arbitrary proportion；Preferably, institute
The extract part stated is cannabis and/or marihuana.
3. preparation method as described in claim 1, which is characterized in that baking described in step (1), parameter are as follows: baking
Temperature is 100-150 DEG C, and the time of baking is 20-80min；The crushing is that hemp extract part is crushed to 10-80 mesh.
4. preparation method as described in claim 1, which is characterized in that extracting parameter described in step (2) includes: the solvent
For ethyl alcohol, the solvent usage is 5-15 times of medicinal material amount, and the extraction time is 1-5 times, and each extraction time is 1-3h, institute
The extracting method stated is selected from: cold-maceration, ultrasonic extraction, reflux extraction and leaching are filtered the group of one or more of method
It closes.
5. preparation method as described in claim 1, which is characterized in that the parameter of extraction described in step (3) includes: described
Extractant is selected from: the combination of one or more of ethyl acetate, n-butanol, n-hexane, petroleum ether and methylene chloride,
The extractant dosage is 1-6 times of medicinal material amount, and the extraction times are 1-3 times.
6. preparation method as described in claim 1, which is characterized in that thickening temperature described in step (2) and/or (3) is
50-70℃。
7. preparation method as described in claim 1, which is characterized in that adjusting pH described in step (4) includes adding to alkalinity
Enter the step of highly basic adjusts pH；Preferably, the highly basic is selected from: in calcium hydroxide, barium hydroxide, potassium hydroxide and sodium hydroxide
A combination of one or more；
Adjusting pH described in step (4) includes the steps that weak acid for adjusting pH is added to acidity；Preferably, the weak acid is selected from:
The combination of one or more of acetic acid, sulfurous acid and phosphoric acid.
8. preparation method as described in claim 1, which is characterized in that alkaline pH described in step (4) is pH10.0-
12.0, preferably pH11.0；
The acid pH in step (4) is pH4.0-5.0, preferably pH4.6.
9. preparation method as described in claim 1, which is characterized in that solvent described in step (5) is selected from: ethyl acetate,
The combination of one or more of n-butanol, n-hexane, petroleum ether and methylene chloride；
Solvent usage described in step (5) is 0.5-2 times of medicinal material amount.
10. preparation method as described in claim 1, which is characterized in that the chromatography of column described in step (5) chromatographic column used is filled out
Material is silica filler, it is preferred that the silica filler is selected from: amorphous silica gel, spherical silica gel and silica white；
Type of elution described in step (5) is to carry out gradient elution to chromatographic column using eluting solvent, it is preferred that the elution
Step includes: first then to obtain target product part with the elution of eluting solvent 2 with the elution removal of impurities of eluting solvent 1.
11. preparation method as claimed in claim 10, which is characterized in that the eluting solvent 1 is selected from: volume ratio 1:1
Acetone-petroleum ether mixed liquor, volume ratio be 1:9 methylene chloride-n-hexane mixed liquor and volume ratio be 1:30 ethyl acetate-
One of heptane mixture；
The dosage of the eluting solvent 1 is 2-8 times of column volume；
The eluting solvent 2 is selected from: the methylene chloride-that acetone-petroleum ether mixed liquor that volume ratio is 7:3, volume ratio are 2:8
N-hexane mixed liquor and volume ratio are one of 1:25 ethyl acetate-heptane mixed liquor；
The dosage of the eluting solvent 2 is 2-8 times of column volume.
12. a kind of cannabinoids extract of the described in any item method preparations of claim 1-11.
13. cannabinoids extract as claimed in claim 12, which is characterized in that THC contains in the cannabinoids extract
Amount existsBelow；
Combination comprising one or more of CBD, CBDV, CBG and THCV in the extract.
14. cannabinoids extract as claimed in claim 13, which is characterized in that in the extract comprising CBD, CBDV,
CBG and THCV, it is preferred that in the extract, CBD content is 55-60%, and CBDV content is 10-13%, and CBG content is 4-
5%, THCV content are 4-5%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710908169.0A CN109568389B (en) | 2017-09-29 | 2017-09-29 | Preparation method of high-purity cannabinol extract |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710908169.0A CN109568389B (en) | 2017-09-29 | 2017-09-29 | Preparation method of high-purity cannabinol extract |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109568389A true CN109568389A (en) | 2019-04-05 |
| CN109568389B CN109568389B (en) | 2022-02-08 |
Family
ID=65914306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710908169.0A Active CN109568389B (en) | 2017-09-29 | 2017-09-29 | Preparation method of high-purity cannabinol extract |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109568389B (en) |
Cited By (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110063987A (en) * | 2019-05-28 | 2019-07-30 | 厦门梓素生物科技有限公司 | A kind of application of the extract of CBD containing cannabidiol in treatment cardiovascular and cerebrovascular disease |
| CN110143855A (en) * | 2019-07-02 | 2019-08-20 | 黑龙江康源生物科技有限公司 | The isolation and purification method of cannabidiol in a kind of industrial hemp |
| CN110183309A (en) * | 2019-07-02 | 2019-08-30 | 黑龙江康源生物科技有限公司 | A kind of method and bateriostatics for extracting bateriostatics from industrial hemp root |
| CN110256206A (en) * | 2019-07-02 | 2019-09-20 | 黑龙江康源生物科技有限公司 | A kind of method of high speed adverse current chromatogram separation and Extraction cannabidiol |
| CN110302559A (en) * | 2019-05-23 | 2019-10-08 | 朱法科 | The remaining minimizing technology of pesticide in Chinese nettle extract |
| CN110304993A (en) * | 2019-05-23 | 2019-10-08 | 朱法科 | The method of chromatography production high-purity cannabidiol |
| CN110330409A (en) * | 2019-07-24 | 2019-10-15 | 汉义生物科技（北京）有限公司 | A kind of preparation method of industrial hemp extract |
| CN110642679A (en) * | 2019-08-27 | 2020-01-03 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110724589A (en) * | 2019-08-27 | 2020-01-24 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110881481A (en) * | 2019-10-30 | 2020-03-17 | 广州市浪奇实业股份有限公司 | Antibacterial composition containing cannabis sativa leaf extract and application thereof |
| CN110922376A (en) * | 2019-07-10 | 2020-03-27 | 朱法科 | Method for producing high-purity tetrahydrocannabinol by chromatography |
| CN111018675A (en) * | 2019-12-10 | 2020-04-17 | 云南罗瑞生物科技有限公司 | Method for efficiently and incrementally extracting cannabidiol |
| CN111592448A (en) * | 2020-04-20 | 2020-08-28 | 周宇平 | Process for separating and purifying hypocannabidiol from industrial hemp |
| CN111848357A (en) * | 2019-04-30 | 2020-10-30 | 黑龙江阳光工业大麻研究院 | Method for preparing high-purity cannabidiol by using ultra-high liquid chromatography |
| CN111848358A (en) * | 2019-04-30 | 2020-10-30 | 黑龙江阳光工业大麻研究院 | Method for preparing high-purity cannabidiol by combining macroporous resin enrichment with dynamic axial compression column system |
| CN111849606A (en) * | 2019-04-30 | 2020-10-30 | 云南汉盟制药有限公司 | Method for preparing hemp oil and hemp oil prepared thereby |
| CN111960923A (en) * | 2019-12-30 | 2020-11-20 | 云南汉盟制药有限公司 | Recycling method of cannabidiol extraction process waste and application thereof |
| CN111956689A (en) * | 2019-12-30 | 2020-11-20 | 云南汉盟制药有限公司 | Chewing composition and preparation method and application thereof |
| CN111961021A (en) * | 2019-12-30 | 2020-11-20 | 云南汉盟制药有限公司 | Separation and purification process of high-purity geranylflavonoid A |
| CN111978157A (en) * | 2020-08-21 | 2020-11-24 | 滇麻生物科技(曲靖)有限公司 | Method for extracting and purifying cannabidiol from industrial cannabis sativa |
| CN112011399A (en) * | 2020-08-21 | 2020-12-01 | 滇麻生物科技(曲靖)有限公司 | Method for preparing polyphenol resin oil from industrial hemp |
| WO2020238642A1 (en) | 2019-05-30 | 2020-12-03 | 汉义生物科技（北京）有限公司 | Inclusion compound containing non-psychoactive cannabinoid and method for preparation thereof |
| CN112062658A (en) * | 2020-08-21 | 2020-12-11 | 滇麻生物科技(曲靖)有限公司 | Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp |
| CN112159311A (en) * | 2019-07-29 | 2021-01-01 | 中国农业科学院麻类研究所 | Extraction and purification method of cannabidiol |
| US11040932B2 (en) | 2018-10-10 | 2021-06-22 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
| CN113009049A (en) * | 2019-12-20 | 2021-06-22 | 浙江华谱新创科技有限公司 | Process for removing THC in full-spectrum hemp extract oil |
| US11084770B2 (en) | 2016-12-07 | 2021-08-10 | Treehouse Biotech, Inc. | Cannabis extracts |
| WO2021232836A1 (en) * | 2020-05-21 | 2021-11-25 | 汉义生物科技（北京）有限公司 | Cannabinoid compounds and application thereof in treatment of parkinson's disease |
| CN113712943A (en) * | 2020-05-25 | 2021-11-30 | 汉义生物科技（北京）有限公司 | Application of hemp full-spectrum oil in treating epilepsy |
| US11202771B2 (en) | 2018-01-31 | 2021-12-21 | Treehouse Biotech, Inc. | Hemp powder |
| CN114053328A (en) * | 2020-08-07 | 2022-02-18 | 汉义生物科技（北京）有限公司 | Method for extracting and purifying total terpene of industrial hemp and preparation |
| CN114539199A (en) * | 2022-02-18 | 2022-05-27 | 云南工麻生物科技有限公司 | Cannabinol derivative compounds and preparation method thereof |
| CN114907191A (en) * | 2021-02-07 | 2022-08-16 | 浙江双子智能装备有限公司 | Hemp impurity removal method |
| CN115010690A (en) * | 2022-06-06 | 2022-09-06 | 云南翰谷生物科技有限公司 | Preparation method of high-purity cannabinol crystal |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739585A (en) * | 2014-02-17 | 2014-04-23 | 辛荣昆 | Technology of extracting dihydrogen cannabinol (CBD) from industrial cannabis sativa |
| CN106278828A (en) * | 2016-08-16 | 2017-01-04 | 云南汉素生物科技有限公司 | A kind of method extracting cannabidiol from industrial hemp floral leaf |
| CN106860492A (en) * | 2017-01-05 | 2017-06-20 | 杭州福斯特光伏材料股份有限公司 | A kind of preparation method of cannabinol compounds |
-
2017
- 2017-09-29 CN CN201710908169.0A patent/CN109568389B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739585A (en) * | 2014-02-17 | 2014-04-23 | 辛荣昆 | Technology of extracting dihydrogen cannabinol (CBD) from industrial cannabis sativa |
| CN106278828A (en) * | 2016-08-16 | 2017-01-04 | 云南汉素生物科技有限公司 | A kind of method extracting cannabidiol from industrial hemp floral leaf |
| CN106831353A (en) * | 2016-08-16 | 2017-06-13 | 云南汉素生物科技有限公司 | A kind of method that cannabidiol is extracted from hemp |
| CN106860492A (en) * | 2017-01-05 | 2017-06-20 | 杭州福斯特光伏材料股份有限公司 | A kind of preparation method of cannabinol compounds |
Non-Patent Citations (1)
| Title |
|---|
| AVITAL SCHURR ET AL: "Cannabis extract, but not △1-tetrahydrocannabinol, inhibits human brain and liver monoamine oxidase", 《GEN. PHARMAC.》 * |
Cited By (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11084770B2 (en) | 2016-12-07 | 2021-08-10 | Treehouse Biotech, Inc. | Cannabis extracts |
| US11202771B2 (en) | 2018-01-31 | 2021-12-21 | Treehouse Biotech, Inc. | Hemp powder |
| US11040932B2 (en) | 2018-10-10 | 2021-06-22 | Treehouse Biotech, Inc. | Synthesis of cannabigerol |
| CN111848357A (en) * | 2019-04-30 | 2020-10-30 | 黑龙江阳光工业大麻研究院 | Method for preparing high-purity cannabidiol by using ultra-high liquid chromatography |
| CN111849606B (en) * | 2019-04-30 | 2021-05-11 | 云南汉盟制药有限公司 | Method for preparing hemp oil and hemp oil prepared thereby |
| WO2020220863A1 (en) * | 2019-04-30 | 2020-11-05 | 云南汉盟制药有限公司 | Method for preparing cannabis sativa l. oil and cannabis sativa l. oil prepared thereby |
| CN111849606A (en) * | 2019-04-30 | 2020-10-30 | 云南汉盟制药有限公司 | Method for preparing hemp oil and hemp oil prepared thereby |
| CN111848358A (en) * | 2019-04-30 | 2020-10-30 | 黑龙江阳光工业大麻研究院 | Method for preparing high-purity cannabidiol by combining macroporous resin enrichment with dynamic axial compression column system |
| CN110302559A (en) * | 2019-05-23 | 2019-10-08 | 朱法科 | The remaining minimizing technology of pesticide in Chinese nettle extract |
| CN110304993A (en) * | 2019-05-23 | 2019-10-08 | 朱法科 | The method of chromatography production high-purity cannabidiol |
| CN110063987A (en) * | 2019-05-28 | 2019-07-30 | 厦门梓素生物科技有限公司 | A kind of application of the extract of CBD containing cannabidiol in treatment cardiovascular and cerebrovascular disease |
| WO2020238642A1 (en) | 2019-05-30 | 2020-12-03 | 汉义生物科技（北京）有限公司 | Inclusion compound containing non-psychoactive cannabinoid and method for preparation thereof |
| CN110256206A (en) * | 2019-07-02 | 2019-09-20 | 黑龙江康源生物科技有限公司 | A kind of method of high speed adverse current chromatogram separation and Extraction cannabidiol |
| CN110183309A (en) * | 2019-07-02 | 2019-08-30 | 黑龙江康源生物科技有限公司 | A kind of method and bateriostatics for extracting bateriostatics from industrial hemp root |
| CN110143855A (en) * | 2019-07-02 | 2019-08-20 | 黑龙江康源生物科技有限公司 | The isolation and purification method of cannabidiol in a kind of industrial hemp |
| CN110922376A (en) * | 2019-07-10 | 2020-03-27 | 朱法科 | Method for producing high-purity tetrahydrocannabinol by chromatography |
| CN110330409B (en) * | 2019-07-24 | 2022-04-19 | 汉义生物科技（北京）有限公司 | Preparation method of industrial hemp extract |
| CN110330409A (en) * | 2019-07-24 | 2019-10-15 | 汉义生物科技（北京）有限公司 | A kind of preparation method of industrial hemp extract |
| CN112159311B (en) * | 2019-07-29 | 2023-09-01 | 中国农业科学院麻类研究所 | Extraction and purification method of cannabidiol |
| CN112159311A (en) * | 2019-07-29 | 2021-01-01 | 中国农业科学院麻类研究所 | Extraction and purification method of cannabidiol |
| CN110642679B (en) * | 2019-08-27 | 2022-07-22 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110724589A (en) * | 2019-08-27 | 2020-01-24 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110642679A (en) * | 2019-08-27 | 2020-01-03 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110724589B (en) * | 2019-08-27 | 2023-01-10 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110881481A (en) * | 2019-10-30 | 2020-03-17 | 广州市浪奇实业股份有限公司 | Antibacterial composition containing cannabis sativa leaf extract and application thereof |
| CN111018675A (en) * | 2019-12-10 | 2020-04-17 | 云南罗瑞生物科技有限公司 | Method for efficiently and incrementally extracting cannabidiol |
| CN113009049A (en) * | 2019-12-20 | 2021-06-22 | 浙江华谱新创科技有限公司 | Process for removing THC in full-spectrum hemp extract oil |
| CN111956689A (en) * | 2019-12-30 | 2020-11-20 | 云南汉盟制药有限公司 | Chewing composition and preparation method and application thereof |
| CN111961021A (en) * | 2019-12-30 | 2020-11-20 | 云南汉盟制药有限公司 | Separation and purification process of high-purity geranylflavonoid A |
| CN111960923B (en) * | 2019-12-30 | 2023-01-03 | 云南汉盟制药有限公司 | Recycling method of cannabidiol extraction process waste and application thereof |
| CN111960923A (en) * | 2019-12-30 | 2020-11-20 | 云南汉盟制药有限公司 | Recycling method of cannabidiol extraction process waste and application thereof |
| CN111592448A (en) * | 2020-04-20 | 2020-08-28 | 周宇平 | Process for separating and purifying hypocannabidiol from industrial hemp |
| WO2021232836A1 (en) * | 2020-05-21 | 2021-11-25 | 汉义生物科技（北京）有限公司 | Cannabinoid compounds and application thereof in treatment of parkinson's disease |
| CN113694049A (en) * | 2020-05-21 | 2021-11-26 | 汉义生物科技（北京）有限公司 | Cannabinoid compounds and their use in treating parkinson's disease |
| CN113694049B (en) * | 2020-05-21 | 2022-11-22 | 汉义生物科技（北京）有限公司 | Cannabinoid compounds and their use in treating parkinson's disease |
| CN113712943A (en) * | 2020-05-25 | 2021-11-30 | 汉义生物科技（北京）有限公司 | Application of hemp full-spectrum oil in treating epilepsy |
| WO2021238242A1 (en) * | 2020-05-25 | 2021-12-02 | 汉义生物科技（北京）有限公司 | Use of full-spectrum hemp oil in treatment of epilepsy |
| CN114053328A (en) * | 2020-08-07 | 2022-02-18 | 汉义生物科技（北京）有限公司 | Method for extracting and purifying total terpene of industrial hemp and preparation |
| CN111978157A (en) * | 2020-08-21 | 2020-11-24 | 滇麻生物科技(曲靖)有限公司 | Method for extracting and purifying cannabidiol from industrial cannabis sativa |
| CN112062658A (en) * | 2020-08-21 | 2020-12-11 | 滇麻生物科技(曲靖)有限公司 | Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp |
| CN112011399A (en) * | 2020-08-21 | 2020-12-01 | 滇麻生物科技(曲靖)有限公司 | Method for preparing polyphenol resin oil from industrial hemp |
| CN114907191A (en) * | 2021-02-07 | 2022-08-16 | 浙江双子智能装备有限公司 | Hemp impurity removal method |
| CN114539199A (en) * | 2022-02-18 | 2022-05-27 | 云南工麻生物科技有限公司 | Cannabinol derivative compounds and preparation method thereof |
| CN115010690A (en) * | 2022-06-06 | 2022-09-06 | 云南翰谷生物科技有限公司 | Preparation method of high-purity cannabinol crystal |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109568389B (en) | 2022-02-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109568389A (en) | A kind of preparation method of high-purity cannabinoids extract | |
| CN110330409A (en) | A kind of preparation method of industrial hemp extract | |
| CN100475243C (en) | Hypoglycemic, antilipenic and hemopathy-treating glutinous rehmannia extract and preparing method thereof | |
| CN101244129B (en) | Lhasa rhubarb extract, preparation method, and application in preparing preparation for treating cardiovascular and cerebrovascular diseases | |
| CN109574810A (en) | Method that is a kind of while extracting CBD and CBDV | |
| CN110051726A (en) | The preparation method and application of general flavone and total starches in a kind of Qingqian Willow leaf | |
| CN101899070A (en) | The preparation method of flavonoid glycoside in the compression leg sharp separation cake of camellia oleifera seeds in a kind of | |
| CN102688431A (en) | Kidney-reinforcing oral liquid and preparation method thereof | |
| CN101085129A (en) | Acorus gramineus total phenylpropanoid extraction and total phenols extraction and method for preparing simultaneously | |
| Zhang et al. | Matrix solid-phase dispersion extraction coupled with HPLC-diode array detection method for the analysis of sesquiterpene lactones in root of Saussurea lappa CB Clarke | |
| CN102293868A (en) | Application of total flavonoids of lilac daphne root to preparation of medicament for reducing blood sugar | |
| CN108530430A (en) | Ester catechin pyrrolidine alkaloid and its preparation method and application | |
| CN104829474B (en) | Method for preparing glycine betaine chemical reference substances from boxthorn leaves | |
| CN104211690B (en) | Method for separating and purifying mangiferin from aquilaria sinensis leaves | |
| CN101912436A (en) | Ultrasonic extraction method of alfalfa saponin | |
| CN102302615B (en) | Effective site group of daphne giraldii nitsche leaf, preparation method, medicinal composition and application thereof | |
| CN101091734A (en) | Method for preparing extractive of pubescent angelica root coumarin | |
| CN101313938B (en) | Magnolia flower volatile oil spray for nose | |
| CN101323605A (en) | Preparation of isobenzofuran ketone compounds | |
| CN104257756B (en) | The application in preparing hypoglycemic medicine of a kind of Cortex Mori fatty oil | |
| CN103760271B (en) | The detection method of brain heart clearing capsule | |
| CN103239435B (en) | Preparation method of gynura divaricata total caffeoylquinic acid and application in antihyperglycemic agent or health-care product | |
| CN103110890B (en) | Effective part of Xierigasiwei (Mongolian medicine) as well as preparation method, quality detection method and application thereof | |
| CN103316087B (en) | Semen Myristicae five tastes effective site and preparation method thereof, quality determining method and application | |
| CN101176755B (en) | Application of meletin-7-0-glycoside in mass control of cudrania tricuspidata or preparations thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |