CN112266321A - Method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa - Google Patents
Method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa Download PDFInfo
- Publication number
- CN112266321A CN112266321A CN202011105865.6A CN202011105865A CN112266321A CN 112266321 A CN112266321 A CN 112266321A CN 202011105865 A CN202011105865 A CN 202011105865A CN 112266321 A CN112266321 A CN 112266321A
- Authority
- CN
- China
- Prior art keywords
- decarboxylation
- cannabidiol
- cannabidiolic acid
- industrial
- microwave radiation
- 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.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Botany (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method for decarboxylation of cannabidiolic acid in industrial cannabis sativa, belongs to the technical field of extraction and purification of plant components, and particularly relates to a pretreatment process method for preparing cannabidiol by cannabidiolic acid decarboxylation. The microwave radiation method is utilized to convert cannabidiolic acid into cannabidiol by decarboxylation. The optimal decarboxylation conditions are that the microwave radiation temperature is 60 ℃, the microwave power is 600W, the microwave radiation time is 30 minutes, the decarboxylation rate of the cannabidiolic acid is more than 98 percent through liquid chromatography analysis, the cannabidiolic acid converted cannabidiol reaches 99 percent, and the cannabidiol structure is analyzed through mass spectrometry. According to the invention, cannabidiol can be simply and efficiently converted by decarboxylating cannabidiolic acid by adopting a microwave radiation method, and compared with a heating decarboxylation method, the method has the advantages of short time, high efficiency, low energy consumption, small environmental pollution and the like, and is suitable for raw material pretreatment in the pharmaceutical field and industrial production.
Description
Technical Field
The invention belongs to the technical field of plant component extraction and purification, and particularly relates to a method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa.
Background
Cannabis sativa L belonging to Magnoliaceae, Urticales, Cannabaceae, Cannabis species, annual herbaceous plant. Cannabis is the most controversial plant in the world, with the principal neutral component being (-) -trans- Δ9-tetrahydrocannabinol (Δ)9-THC) can cause hallucinogenic effects and are therefore required to be strictly regulated. The hemp plant is widely distributed around the world, and has been applied to the fields of textile, paper making, composite materials, medicines and the like along with the continuous and deep excavation of hemp plant resources in recent years. The hemp with the Tetrahydrocannabinol (THC) content of less than 0.3 percent is internationally called industrial hemp, which is also called hemp, jute, hemp, etc. in China. The industrial hemp planting and the flower and leaf processing in China need approval permission of local public security organs, and two provinces of Yunnan (2010) and Heilongjiang (2017) have been approved to develop the industrial hemp industry. According to the statistics of the food and agriculture organization of the united nations, europe, china, korea and russia are the main industrial hemp production areas in the world, wherein the planting area of china is the largest and occupies about half of the planting area of the industrial hemp in the world.
The active ingredients in the cannabis plant include cannabinoids and non-cannabinoids, and the amount and active ingredients of cannabinoids are large. Since 1940, at least 110 cannabinoid components have been isolated from cannabis plants. The first cannabinoid major psychoactive ingredient, Δ, isolated by Raphael M in 19649-THC, the isolation of which is an important breakthrough for the structural resolution of the active cannabinoid component. The active cannabinoid components also include Cannabidiol (CBD), Cannabinol (CBN) and Cannabigerol (CBG), as well as cannabinoid acids such as tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA) and cannabigerolic acid (CBGA), and have significant potential in clinical treatment of disease. The CBD and THC molecules are poorly biosynthesized in the cannabis plant, but rather the CBDA and THCA molecules produced by the cannabis plant biosynthesis undergo decarboxylation reactions to yield the corresponding decarboxylated (or neutral) products. THC has hallucinogenic addiction, so that the application of THC is limited, and CBD has quite different active effects with THC, is a non-addictive active component and has no neurotoxicity. Research shows that CBD has important medicinal value, shows good pharmacological activity in the fields of epilepsy treatment, neuroprotection, multiple sclerosis, rheumatoid arthritis, tumor treatment, smoking cessation and the like, and has very good application prospect. Especially, the CBD drugs Sativex and epididolex proposed by GW company are very obvious in curative effect on treating multiple sclerosis and childhood paroxysmal epilepsy, dozens of drugs with CBD as a main active ingredient in the clinical experimental development stage exist, and cannabinoids have become research hotspots in the pharmaceutical field.
At present, the extraction of active ingredients of cannabinoid mainly comprises solvent extraction method and supercritical CO2The fluid extraction method and the subcritical fluid extraction method are three methods, the cannabinoid monomer purification method is a column chromatography technology, and the cannabinoid monomers with different contents are purified by selecting chromatography fillers. The application publication No. CN104277917A discloses a method for extracting cannabidiol resin oil from industrial hemp and an extraction device thereof, and the main procedures comprise the steps of screening, baking, leaching, column chromatography and the like. The application publication No. CN10967865A patent disclosesAccording to the method for separating the cannabidiol, the extract is dissolved in a mixed solvent of n-hexane and ethyl acetate, and a CBD monomer with the purity of 84-90% is prepared. The application publication No. CN109646992 discloses a method for extracting cannabidiol concentrate from industrial hemp, alkaline water is used for extracting, adjusting acid and precipitating, and the concentrate with the CBD content of 41.3-43.2% is finally obtained after concentration. Application publication No. CN109627148 discloses a method for preparing cannabidiol, which utilizes eutectic solvent extraction, crude extract is separated by resin, CBD recovery rate is 81.46%, and purity is 28.93%. The application publication No. CN109369344A discloses a method for separating and extracting cannabidiol from industrial cannabis sativa, which comprises the steps of soaking in 95% ethanol/water solution, carrying out ultrasonic heat extraction, and separating and purifying extracts by using a normal phase column and a reverse phase column, wherein the purity of CBD is 92-98%. Application publication No. CN109232191A discloses a method for extracting cannabidiol from industrial hemp leaves, drying and pulverizing industrial hemp leaves, adding cell wall decomposition enzyme cellulase and pectinase for hydrolysis, and obtaining CBD solution for chromatographic analysis. The application publication No. CN109053388A discloses a method for extracting cannabidiol, which comprises drying industrial hemp flowers and leaves, performing countercurrent leaching by using a countercurrent leaching extraction device, performing gradient elution by using a chromatographic column, and preparing a CBD product by using a recrystallization technology. The application publication No. CN108998248A discloses a preparation method of industrial hemp flower and leaf absolute oil rich in cannabidiol, wherein flowers and leaves of industrial hemp are dried and crushed, hemp powder is soaked in edible oil to obtain hemp soaking oil, and the hemp soaking oil is extracted by food-grade ethanol and concentrated to obtain hemp oil. Application publication No. CN107011125A discloses a method for enriching cannabidiol, industrial cannabis leaves raw material is dried for 0.5-4 hours at 120 ℃, carbon dioxide supercritical extraction is carried out for 1-9 hours at 30-55 ℃ and 13-30 MPa to obtain cannabinoid crude extract, column chromatography is utilized for gradient elution or isocratic elution, and the eluted fraction of cannabidiol is collected. CBD in industrial hemp flowers and leaves exists in the form of cannabidiolic acid (CBDA) precursor, and CBDA is converted into CBD molecules only by decarboxylation at high temperature. The pretreatment of the industrial big fried dough twist leaf raw material in the patent needs heating decarboxylation and extract decarboxylation steps, and industrial hemp leaves or extracts need to be subjected to the steps of heating decarboxylation and extract decarboxylationThe object is roasted in a baking oven at high temperature for a period of time for decarboxylation and conversion, a large amount of energy consumption is needed, meanwhile, a certain loss is brought to the content of CBDA and CBD under the high-temperature condition, and a new technology and a new method for improving the CBDA decarboxylation process in industrial hemp are urgently needed.
Disclosure of Invention
The invention aims to solve the problem of decarboxylation and transformation of cannabidiolic acid in actual work, develop cannabinoid active ingredients in industrial cannabis and provide a method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa comprises the following steps:
the method comprises the following steps: treating industrial hemp flowers and leaves: harvesting industrial hemp flowers and leaves in the mature period, washing the flowers and leaves with water to remove impurities, drying the flowers and leaves at the natural temperature, crushing, packaging and storing at a low temperature for later use; the pretreatment step has the function of cleaning and being beneficial to the uniform energy transfer of microwave radiation cracking;
step two: the microwave radiation cannabidiolic acid decarboxylation method comprises the following steps: weighing 100g of the treated industrial hemp flower and leaf sample, and putting the sample into a 1L raw material kettle, wherein the experimental parameters are set to be 40-60 ℃ of microwave radiation temperature, 300-. The microwave radiation decarboxylation process is that cannabidiolic acid molecules are decarboxylated under the action of microwave radiation energy and temperature → cannabidiol molecules. because-COO-is an electron-withdrawing group, the electronegativity is large, the polar end generates dipole steering and interface polarization in a microwave field, and the carboxyl end is preferentially heated, so that the decarboxylation of the cannabinoid acid is promoted.
Further, in the step one, the water content of the dried flowers and leaves is less than 5%.
Further, in the second step, the microwave radiation temperature is 40 ℃, 50 ℃ or 60 ℃.
Further, in the second step, the microwave power is 300W, 450W, 600W or 800W.
Compared with the prior art, the invention has the beneficial effects that:
1. compared with the traditional heating decarboxylation method, the microwave radiation time has the advantages of short time, high efficiency and the like.
2. Compared with the traditional heating decarboxylation method, the microwave radiation energy consumption has the advantages of low energy consumption, low production cost and the like.
3. Compared with the traditional heating decarboxylation mode, the microwave radiation temperature has the advantages of low operation temperature, less release of volatile molecules, less peculiar smell, less environmental pollution and the like.
Drawings
FIG. 1 is a raw material liquid chromatography diagram;
FIG. 2 is a liquid chromatography analysis of a feedstock after microwave irradiation;
FIG. 3 is a graph of cannabidiol mass spectrometry after microwave irradiation;
FIG. 4 is an analytical chart of a decarboxylation experiment under heating at 50 ℃;
FIG. 5 is an experimental analysis chart of decarboxylation under heating at 60 ℃;
FIG. 6 is an analytical chart of decarboxylation experiment under heating at 80 ℃.
Detailed Description
The technical solutions of the present invention are further described below with reference to the drawings and the embodiments, but the present invention is not limited thereto, and modifications or equivalent substitutions may be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
The invention provides a simple and efficient cannabidiolic acid decarboxylation method, which utilizes a microwave radiation technology to realize efficient cannabidiolic acid decarboxylation and transformation of cannabidiol. The method reduces energy consumption in the conventional heating decarboxylation process, shortens decarboxylation reaction time, reduces heat loss in the cannabidiol acid heating decarboxylation process, and improves cannabidiolic acid decarboxylation efficiency and conversion rate.
Example 1:
a method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa comprises the following steps:
the method comprises the following steps: treating industrial hemp flowers and leaves: harvesting industrial hemp flowers and leaves in the mature period, washing the flowers and leaves with water to remove impurities, drying the flowers and leaves at the natural temperature, crushing, packaging and storing at a low temperature for later use; the pretreatment step has the function of cleaning and being beneficial to the uniform energy transfer of microwave radiation cracking;
step two: the microwave radiation cannabidiolic acid decarboxylation method comprises the following steps: 100g of the treated industrial hemp flower and leaf sample is weighed and put into a 1L raw material kettle, and the experimental parameters are set to be 40 ℃ of microwave radiation temperature, 300W of microwave power and 30 minutes of time.
Detecting the content of cannabidiol: the specific chromatographic conditions are that a chromatographic column: c18(150 mm. times.4.6 mm, 5 μm); mobile phase: hexanitrile-water (78: 22); flow rate: 0.7 mL/min-1(ii) a Detection wavelength: 230 nm; column temperature: 30 ℃; sample introduction amount: 10 μ L. Under the chromatographic condition, the theoretical plate number of cannabidiol and cannabidiolic acid is not lower than 2500, and the separation degree and tailing factors meet the content determination requirements, so that a graph 1 and a graph 2 are obtained. Characterization of cannabidiol structure: the structural characterization of the product is carried out by liquid chromatography and liquid chromatograph-mass spectrometer equipment, and the obtained figure 3 shows that 315.2 is a cannabidiol molecular ion peak, 259.1, 193.1 and 135.2 are main fragment peaks of cannabidiol molecules, and the structural characterization of the product prepared by the method shows that the decarboxylation product prepared by the method has a correct structure.
Example 2:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 40 ℃ for microwave irradiation, 450W for microwave power, and 30 minutes for time.
Example 3:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 40 ℃ for microwave irradiation, 600W for microwave power, and 30 minutes for time.
Example 4:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 40 ℃ for microwave irradiation, 800W for microwave power, and 30 minutes for time.
Example 5:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 50 ℃ for microwave irradiation, 300W for microwave power, and 30 minutes for time.
Example 6:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 50 ℃ for microwave irradiation, 450W for microwave power, and 30 minutes for time.
Example 7:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 50 ℃ for microwave irradiation, 600W for microwave power, and 30 minutes for time.
Example 8:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 50 ℃ for microwave irradiation, 800W for microwave power, and 30 minutes for time.
Example 9:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 60 ℃ for microwave irradiation, 300W for microwave power, and 30 minutes for time.
Example 10:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 60 ℃ for microwave irradiation, 450W for microwave power, and 30 minutes for time.
Example 11:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 60 ℃ for microwave irradiation, 600W for microwave power, and 30 minutes for time.
Example 12:
the difference between this example and example 1 is that in the second step, the experimental parameters were set to 600 ℃ for microwave irradiation, 800W for microwave power, and 30 minutes for time.
Comparative example 1:
a method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa comprises the following steps:
the method comprises the following steps: treating industrial hemp flowers and leaves: harvesting industrial hemp flowers and leaves in the mature period, washing the flowers and leaves with water to remove impurities, drying the flowers and leaves at the natural temperature, crushing, packaging and storing at a low temperature for later use; the pretreatment step has the function of cleaning and being beneficial to uniform heat transfer;
step two: the heating decarboxylation method of the cannabidiolic acid comprises the following steps: 100g of the treated industrial hemp flower and leaf sample is weighed and placed into a forced air drying oven, and the experimental parameters are set to be 50 ℃ for 180 minutes.
Comparative example 2:
the comparative example differs from comparative example 1 in that in step two, the experimental parameters were set at 60 ℃ for 180 minutes.
Comparative example 3:
the comparative example differs from comparative example 1 in that in step two, the experimental parameters were set at 80 ℃ for 180 minutes.
FIGS. 4 to 6 are experimental analysis graphs obtained in comparative examples 1 to 3, and in example 11 of the present invention, the decarboxylation rate of cannabidiolic acid was 98% or more, and the conversion rate was 99%, and compared with the decarboxylation by heating, the decarboxylation time, decarboxylation rate, and conversion rate were all significantly improved.
Claims (4)
1. A method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa is characterized by comprising the following steps: the method specifically comprises the following steps:
the method comprises the following steps: treating industrial hemp flowers and leaves: harvesting industrial hemp flowers and leaves in the mature period, washing the flowers and leaves with water to remove impurities, drying the flowers and leaves at the natural temperature, crushing, packaging and storing at a low temperature for later use;
step two: the microwave radiation cannabidiolic acid decarboxylation method comprises the following steps: weighing 100g of the treated industrial hemp flower and leaf sample, and putting the sample into a 1L raw material kettle, wherein the experimental parameters are set to be 40-60 ℃ of microwave radiation temperature, 300-.
2. The method of claim 1 for the decarboxylation of cannabidiolic acid to cannabidiol in industrial cannabis sativa, wherein the method comprises: in the first step, the water content of the dried flowers and leaves is less than 5%.
3. The method of claim 1 for the decarboxylation of cannabidiolic acid to cannabidiol in industrial cannabis sativa, wherein the method comprises: in the second step, the microwave radiation temperature is 40 ℃, 50 ℃ or 60 ℃.
4. The method of claim 1 for the decarboxylation of cannabidiolic acid to cannabidiol in industrial cannabis sativa, wherein the method comprises: in the second step, the microwave power is 300W, 450W, 600W or 800W.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011105865.6A CN112266321A (en) | 2020-10-15 | 2020-10-15 | Method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011105865.6A CN112266321A (en) | 2020-10-15 | 2020-10-15 | Method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112266321A true CN112266321A (en) | 2021-01-26 |
Family
ID=74338651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011105865.6A Pending CN112266321A (en) | 2020-10-15 | 2020-10-15 | Method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112266321A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112961036A (en) * | 2021-03-01 | 2021-06-15 | 云南瀚通生物科技有限公司 | Extraction and purification method of high-purity cannabidiol |
| CN113652306A (en) * | 2021-09-03 | 2021-11-16 | 黑龙江省科学院高技术研究院 | Extraction method for improving cannabidiol content in hemp essential oil |
| WO2024088287A1 (en) * | 2022-10-27 | 2024-05-02 | 云南麻叶生物科技有限公司 | Decarboxylation method for industrial hemp flowers and leaves |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337586A (en) * | 2017-08-28 | 2017-11-10 | 黑龙江省科学院大庆分院 | A kind of method of extraction purification cannabidiol in fiber crops from the Chinese |
| CN108949363A (en) * | 2018-09-26 | 2018-12-07 | 常德华馥生物技术有限公司 | A kind of Solventless Extraction Process of industrial hemp floral leaf essential oil |
| CN109475586A (en) * | 2016-06-29 | 2019-03-15 | 康纳塞斯创新公司 | The cannabis resin of decarboxylation, its purposes and the method for preparing it |
| CN109970518A (en) * | 2019-05-06 | 2019-07-05 | 开远伯盛科技有限公司 | A method of extracting cannabidiol from industrial hemp |
| CN110041171A (en) * | 2019-05-31 | 2019-07-23 | 黑龙江阳光工业大麻研究院 | A method of extracting cannabidiol from industrial hemp leaf |
| CN110317126A (en) * | 2019-07-02 | 2019-10-11 | 黑龙江康源生物科技有限公司 | A kind of method and system for extracting cannabidiol in industrial hemp with microwave-assisted Subcritical Water Extraction technology |
| CN110803982A (en) * | 2019-11-29 | 2020-02-18 | 云南绿新生物药业有限公司 | Microwave-assisted extraction of cannabidiol and preparation method thereof |
-
2020
- 2020-10-15 CN CN202011105865.6A patent/CN112266321A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109475586A (en) * | 2016-06-29 | 2019-03-15 | 康纳塞斯创新公司 | The cannabis resin of decarboxylation, its purposes and the method for preparing it |
| CN107337586A (en) * | 2017-08-28 | 2017-11-10 | 黑龙江省科学院大庆分院 | A kind of method of extraction purification cannabidiol in fiber crops from the Chinese |
| CN108949363A (en) * | 2018-09-26 | 2018-12-07 | 常德华馥生物技术有限公司 | A kind of Solventless Extraction Process of industrial hemp floral leaf essential oil |
| CN109970518A (en) * | 2019-05-06 | 2019-07-05 | 开远伯盛科技有限公司 | A method of extracting cannabidiol from industrial hemp |
| CN110041171A (en) * | 2019-05-31 | 2019-07-23 | 黑龙江阳光工业大麻研究院 | A method of extracting cannabidiol from industrial hemp leaf |
| CN110317126A (en) * | 2019-07-02 | 2019-10-11 | 黑龙江康源生物科技有限公司 | A kind of method and system for extracting cannabidiol in industrial hemp with microwave-assisted Subcritical Water Extraction technology |
| CN110803982A (en) * | 2019-11-29 | 2020-02-18 | 云南绿新生物药业有限公司 | Microwave-assisted extraction of cannabidiol and preparation method thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112961036A (en) * | 2021-03-01 | 2021-06-15 | 云南瀚通生物科技有限公司 | Extraction and purification method of high-purity cannabidiol |
| CN113652306A (en) * | 2021-09-03 | 2021-11-16 | 黑龙江省科学院高技术研究院 | Extraction method for improving cannabidiol content in hemp essential oil |
| CN113652306B (en) * | 2021-09-03 | 2023-12-26 | 黑龙江省科学院高技术研究院 | Extraction method for improving cannabidiol content in hemp essential oil |
| WO2024088287A1 (en) * | 2022-10-27 | 2024-05-02 | 云南麻叶生物科技有限公司 | Decarboxylation method for industrial hemp flowers and leaves |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112266321A (en) | Method for preparing cannabidiol by decarboxylation of cannabidiolic acid in industrial cannabis sativa | |
| CN101914304B (en) | Method for extracting blueberry anthocyanin | |
| CN101773593B (en) | Method for preparing antioxidative active extractive of sweet potato leaves | |
| CN110304994A (en) | A method of extracting high-purity cannabidiol from industrial hemp | |
| CN108409813A (en) | A method of continuously extracting flaxseed gum and flax lignan from flaxseed meal | |
| CN111249321B (en) | Method for simultaneously preparing black currant polyphenol and polysaccharide | |
| CN103420970A (en) | Method for extracting and purifying anthocyanidin | |
| WO2020228786A1 (en) | Industrialized method for rapidly and efficiently extracting xanthophyll and quercetagetin | |
| CN102061220B (en) | Method for preparing onion functional components by using double-stage extraction based on subcritical water and solvent method | |
| CN104710391A (en) | Method for extracting luteolin and beta-sitosterol from peanut shells | |
| CN103432562A (en) | Method for extracting fresh ginger polyphenol from fresh ginger | |
| CN104173438A (en) | Preparation method of general flavone of purple perilla | |
| CN105924495B (en) | High-efficiency preparation method of high-purity flaxseed protein | |
| CN102040579A (en) | Method for extracting luteolin from peanut roots, stems, leaves and shells | |
| CN100425247C (en) | Refining ganoderam lucidum spore oil and method for preparing same | |
| Sanz et al. | Valorisation of Camellia sinensis branches as a raw product with green technology extraction methods | |
| KR101617432B1 (en) | Method for preparing Red Ginseng extracts containing abundant ginsenosid Rg3 | |
| CN102031116A (en) | New method for preparing rosemary natural antioxidant | |
| CN113817539A (en) | Method for extracting peanut meal oil by using low-temperature continuous phase change | |
| CN105712896A (en) | Method for efficiently preparing macamides monomers from Lepidium meyenii | |
| CN101704729A (en) | Method for extracting resveratrol and polydatin in grape seeds | |
| CN101838178A (en) | Preparation method of lycopene | |
| CN104000935A (en) | Method for extracting anti-oxidative phenolic acids from potato peel slag | |
| CN103239546A (en) | Method for extracting general flavone from litchi shells | |
| CN103432205A (en) | Novel method for extracting high-purity lotus leaf flavone |
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 |