CN110204426A - A kind of preparation method and water solubility CBD of water solubility CBD - Google Patents
A kind of preparation method and water solubility CBD of water solubility CBD Download PDFInfo
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- CN110204426A CN110204426A CN201910590732.3A CN201910590732A CN110204426A CN 110204426 A CN110204426 A CN 110204426A CN 201910590732 A CN201910590732 A CN 201910590732A CN 110204426 A CN110204426 A CN 110204426A
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- cyclodextrin
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- 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
Abstract
The invention discloses the preparation methods of water solubility CBD a kind of, belong to CBD and extract manufacture field, this method comprises: 1) liphophilic solvents are dissolved in ethyl alcohol, form the first solution containing liphophilic solvents and ethyl alcohol；2) CBD extract is dissolved in the first solution, CBD association liquid is made；3) CBD is associated into liquid and the second solution containing cyclodextrin mixes, and CBD is filled into cyclodextrin gap, the water-soluble CBD containing solvent is made；4) solvent is removed, obtains water-soluble CBD, the invention also discloses the water-soluble CBD products prepared by the above method.
Description
Technical field
The present invention relates to industrial hemp fields.
Background technique
CBD, i.e. cannabidiol, are most important active constituents in hemp, and secondary metabolite is mainly mentioned by hemp floral leaf
Purifying is taken to be prepared.CBD molecular formula: C21H30O2, molecular weight: 314.46, light yellow resin or crystalline solid are not soluble in water,
Readily soluble ethyl alcohol, methanol, ethyl acetate, petroleum ether and chloroform and 10% sodium hydroxide, fusing point are 66~67 DEG C, the molecule of CBD
Structure is as shown in Fig. 1.
CBD is with multiple pharmacological effect: (a) CBD has one for the inhibition of glioma, leukaemia and prostate cancer
Determine effect.CBD has neuroprotection, can reduce the pain of epilepsy, and can play inhibition effect for intractable epilepsy
Fruit reduces the frequency of attack of epilepsy.(b) anti-inflammatory, anti-oxidant.(c) nausea, vomiting.(d) hepatoprotective effect: CBD can be to ischemic
Property hepatic injury and chronic alcoholism caused by hepatic injury play corresponding protective effect, can mitigate because long-term alcohol cause
Hepatic injury (raising etc. including liver transaminase levels).(e) adjust metabolism, enhancing is immunized: regulation inflammatory factor is horizontal, inhibits
The generation of interferon, to improve metabolism and be immunized；It simultaneously can to the treatment aspect of the control of diabetes or early diabetes
It plays a role.Correlative study also turns out that arthritis can be controlled by being injected intraperitoneally or take orally CBD, and can be relieved rheumatoid joint
The pain that inflammation causes.
These physiological actions that CBD has, can be applied to the industries such as drug, food and cosmetics.But due to
The water-soluble problem of CBD, currently, the application of CBD is greatly limited.
Currently, the application and addition of CBD, after mostly dissolving using organic solvent or 10% sodium hydroxide solution, then carry out phase
The subsequent operation of pass, this process will cause poisonous and hazardous dissolvent residual, or introduce new impurity, influence CBD product
Quality.CBD is not soluble in water, significantly limits CBD and is added in food, and is added in cosmetics, can not be used as pulvis
Or particle is directly added into drug.These limit the great potential for all preventing CBD from giving full play to its bioactivity, are market
Massive losses.
Summary of the invention
It is an object of the invention to: in view of the above problems, the preparation method of water solubility CBD a kind of is disclosed, made
Standby CBD has good water solubility, can be widely used in the industries such as food and drug.
Present embodiment discloses the preparation methods of water solubility CBD a kind of, this method comprises:
1) liphophilic solvents are dissolved in ethyl alcohol, form the first solution containing liphophilic solvents and ethyl alcohol；
2) CBD extract is dissolved in the first solution, and CBD association liquid is made；
3) CBD is associated into liquid and the second solution containing cyclodextrin mixes, and made CBD be filled into cyclodextrin gap and work as
In, the water-soluble CBD solution containing solvent is made；
4) solvent is removed, water-soluble CBD is obtained.
Extract containing CBD is dissolved in the first solution by the present invention, and association liquid is made first, and secondly will associate liquid
It is mixed with cyclodextrin, so that CBD molecule is substantially filled in cyclodextrin gap.If directly the first solution, CBD and ring pasted
Essence mixing, the ethyl alcohol and liphophilic solvents that will lead in the first solution can be directly filled into the hole of cyclodextrin, cannot be effective
By CBD embed or reduce CBD embedding efficiency；Meanwhile by the first solution, CBD and cyclodextrin directly mix filling if,
When CBD simple substance is not completely dissolved, it is bulky crystal or sticky medicinal extract, cannot be filled into cyclodextrin hole, also can make CBD not
It can embed or reduce embedding efficiency.Therefore it prepares CBD association liquid first in the present invention, CBD is dissolved into small-molecule substance
Afterwards, it is secondly mixed with cyclodextrin solution, CBD small molecule, which is filled into hole, could improve embedding efficiency.
Meanwhile when preparing the first solution as solvent dissolution CBD, the present invention is dissolved with oleophylic in ethanol first
Property solvent, the liphophilic solvents aloow the water-soluble CBD product of preparation not influence CBD primary characteristic, paste with ring
Essence combination, collaboration increases the water solubility of CBD of the present invention, water-soluble up to 10%-30% compared with CBD；It is solid to be easy to subsequent preparation
Body preparation.
Cyclodextrin of the invention does not influence the final quality of the CBD of association, improves the mouthfeel of associated matter；Increase is cooperateed with simultaneously
The water solubility of the CBD of association helps subsequent to prepare many kinds of solids preparation；When not adding antioxidant, cyclodextrin
Package action is avoided that various oxidation possibilities of the invention, extends onset time of the invention.
CBD be it is hydrophobic, in the solution of the present invention, liphophilic solvents and ethyl alcohol will be dissolved in first, is made with second
Pure and mild oil-based solvent mixture, liphophilic solvents play dissolution assistant effect.In lipophilicity of the preferred embodiment described in
Solvent selects the phosphatide or phosphoglyceride of phosphorous acid glyceride, and phosphoglyceride, cyclodextrin are common Edible materials, for a long time
It takes highly-safe, is suitble to prepare functional food；Raw material sources are extensive, and component collocation is simple, solid pharmaceutical preparation supplementary product kind and
Dosage is few, clear efficacy, can combine a variety of dosage form products of production.
In other preferred embodiment, liphophilic solvents are rilanit special, it was found that, hydrogenated castor
Oil not only help solubilization, moreover it is possible to prevent subsequent CBD solution from precipitating, play the role of stabilizer, can save process
With the purity for reducing cost and raising CBD.Further, rilanit special can play emulsifier, stabilizer and cosolvent
Effect, can enable CBD that stable solvent swelling state is presented in water when CBD is dissolved in water.It cooperates with and increases with cyclodextrin
The strong dissolution rate of CBD, release improve the dissolution situation of fat-soluble CBD in water, are not influencing CBD primary characteristic
In the case of, the type form and its functional application range of CBD solid pharmaceutical preparation are widened, and adding for chemicals can be reduced
Enter, has saved process and cost.In preferred scheme, rilanit special is pharmaceutical grade, can be used for cosmetics and drug, makes
With highly-safe, enable to solid pharmaceutical preparation supplementary product kind and dosage few so that the cosmetics and drug of preparation more the effect of
It is clear.
CBD extract of the invention is the product or product containing CBD extracted from industrial hemp, and specifically, CBD is mentioned
Taking object is CBD simple substance or full pedigree essential oil or hemp essential oil or industrial hemp floral leaf extract (CBD content > 40%).
Preferably, the mass ratio of liphophilic solvents and ethyl alcohol is 1:10~1:20 in the first solution.
In some preferred schemes, the liphophilic solvents select soybean lecithin, with edibility, more excellent
In the scheme of choosing, the mass ratio of the soybean lecithin and CBD is (7-35): 1, as the optimal selection of aforementioned proportion range,
The mass ratio of soybean lecithin and CBD are 14:1.
The second solution of cyclodextrin of the present invention is preferably the saturated solution of cyclodextrin and water mixing, of the present invention
Cyclodextrin is one or more of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, be made corresponding single cyclodextrin solution or
The mixed liquor of person's difference cyclodextrin composition, in the preferred scheme, the cyclodextrin includes gamma-cyclodextrin, specifically
It may include pure gamma-cyclodextrin, gamma-cyclodextrin and alpha-cyclodextrin, gamma-cyclodextrin and beta-cyclodextrin, gamma-cyclodextrin and alpha-cyclodextrin
Beta-cyclodextrin, wherein in the scheme of latter three, the ratios of gamma-cyclodextrin and other cyclodextrin be (1:2)-(1:10), more into
In the preferred embodiment of one step, the ratio of gamma-cyclodextrin and other cyclodextrin is 1:4.
The present invention can be used a variety of methods that liphophilic solvents are dissolved in ethyl alcohol, as a kind of wherein preferred side
Case, the present invention use the scheme of heating stirring mix liphophilic solvents and ethyl alcohol, more preferably use
Electromagnetic heating blender carries out heating stirring, and preferred stirring rate is 500r/min, and whipping temp is 40-60 DEG C, stirring
Time is 0.5-4h, is mixed, is filtered later, selection more preferably, and whipping temp is 50 DEG C, and mixing time is
0.5h can make the CBD of preparation have maximum solubility.
The present invention can be used a variety of methods that CBD extract is dissolved in the first solution, and CBD association liquid is made,
As a kind of wherein preferred scheme, the present invention uses the scheme of heating stirring dissolve CBD extract
In the first solution, heating stirring is more preferably carried out using electromagnetic heating blender, preferred stirring rate is 500r/
Min, whipping temp are 40-60 DEG C, mixing time 2-4h, are mixed, are filtered later, selection more preferably, stirring
Temperature is 50 DEG C, mixing time 4h, and the CBD of preparation can be made to have maximum solubility.
As the further preferred of above scheme, the present invention can be used a variety of methods that CBD is made adequately to be filled into ring paste
Smart gap, and the solution of water-soluble CBD is formed, the scheme of heating stirring is used as wherein a kind of preferred scheme, the present invention
Can preferably make CBD adequately be filled into cyclodextrin gap, more preferably heated using electromagnetic heating blender
Stirring, preferred stirring rate are 500r/min, and whipping temp is 40-60 DEG C, and mixing time 2-4h is mixed later
Even, filtering, selection more preferably, whipping temp are 50 DEG C, mixing time 4h, and the CBD of preparation can be made to have most
Big solubility.
Preferably, the mass ratio of CBD extract and the first solution is 1:(40~200).
The present invention can be used a variety of conventional methods and remove solvent in step 4, and the solvent of removal is water and ethyl alcohol, specific
Embodiment in, remove solvent use: be placed in spray dryer, be spray-dried, obtain water-soluble CBD product, wherein water
Dissolubility CBD product includes liphophilic solvents and cyclodextrin, and the kind of liphophilic solvents and cyclodextrin is according to preparation side in CBD product
In method depending on the kind of liphophilic solvents and cyclodextrin.
It is precipitated in CBD solution in order to prevent, in the preferred scheme, stabilizer is added in step 3 so that suppression
There is sediment in CBD solution processed, preferably, stabilizer selects hydroxypropyl cellulose sodium, polyethylene glycol, polyvinylpyrrolidone
It is one or more.
The invention also discloses a kind of water solubility CBD, and according to the method described in the present invention and preferably prepared by scheme, institute
The CBD stated includes liphophilic solvents, cyclodextrin.
Detailed description of the invention
Fig. 1 is the molecular structure of CBD；
Fig. 2 is the result figure of gamma-cyclodextrin dosage experiment of single factor；
Fig. 3 is the result figure of gamma-cyclodextrin accounting experiment of single factor；
Fig. 4 is the result figure of soybean lecithin dosage experiment of single factor；
Fig. 5 is the result figure of whipping temp and mixing time experiment of single factor.
Specific embodiment
With reference to the accompanying drawing, the present invention is described in detail.
Water-soluble CBD solubility test method:
Using octadecylsilane chemically bonded silica as filler；With one 0.05% phosphoric acid water (70:30) of acetonitrile for mobile phase；Inspection
Survey wavelength is 220nm.Number of theoretical plate is calculated by the peak CBD should be not less than 10000.
Take CBD reference substance appropriate, it is accurately weighed, add methanol that solution of every 1ml containing 0.1mg is made to get reference substance solution.
CBD reference substance solution is successively diluted in proportion, obtains the CBD reference substance solution of various concentration
In 100mL water, water solubility CBD is excessively added；It is shaken at 37 DEG C for 24 hours, filters to take clear filtrate；Take 1mL clear
Filtrate is shaken up with methanol dilution to 10mL to get test solution.
It is accurate respectively to draw reference substance solution and each 10 μ l of test solution, inject liquid chromatograph, measurement to get.
Standard curve regression equation: Y=97494X+102040, R2=0.9997.
Embodiment 1: present embodiment discloses a kind of water solubility CBD, the preparation method is as follows:
(1) CBD simple substance 1kg, HEL-40 18.0kg, cyclodextrin 1.8kg, 95% ethyl alcohol 4.0L, distilled water 35.0L are weighed；
(2) by HEL-40 18.0kg, 95% ethyl alcohol 4.0L, it is placed in electromagnetic heating blender, stirring rate 500r/min,
It 50 DEG C of heating temperature, mixing time 2h, mixes, filtering, obtains rilanit special-alcohol mixeding liquid；
(3) it by CBD simple substance 1kg, rilanit special-alcohol mixeding liquid, is placed in electromagnetic heating blender, stirring rate
500r/min, 50 DEG C of heating temperature, the association time is 2h, obtains CBD association liquid；
(4) it by obtained CBD association liquid and 35.0L cyclodextrin saturated aqueous solution, is placed in electromagnetic heating blender, stirs
Rate 500r/min, 50 DEG C of heating temperature, stirs 3h, is uniformly mixed, and filtering obtains water-soluble CBD；
(5) the water-soluble CBD that will be obtained, is placed in spray dryer, and spray drying obtains water-soluble CBD product.Through examining
It surveys, the water solubility of water solubility CBD product obtained above is 18%.
A kind of embodiment 2: scheme two: water solubility CBD, the component comprising following quality: CBD simple substance 1kg, soybean lecithin
14.0kg, cyclodextrin 1.8kg.
(1) CBD simple substance 1kg is weighed, soybean lecithin 14.0kg, cyclodextrin 1.8kg, 95% ethyl alcohol 4.0L, distilled water
35.0L, a small amount of polyethylene glycol；
(2) by soybean lecithin 14.0kg, 95% ethyl alcohol 4.0L, polyethylene glycol, electromagnetic heating blender, stirring rate are placed in
500r/min, mixes, filtering, obtains phosphatide alcohol mixeding liquid by 50 DEG C of heating temperature, mixing time 2h；
(3) it by CBD simple substance 1kg, phosphatide alcohol mixeding liquid, is placed in electromagnetic heating blender, stirring rate 500r/min,
50 DEG C of heating temperature, the association time is 2h, obtains CBD association liquid；
(4) it by obtained CBD association liquid and 35.0L cyclodextrin saturated aqueous solution, is placed in electromagnetic heating blender, stirs
Rate 500r/min, 50 DEG C of heating temperature, stirs 3h, is uniformly mixed, and filtering obtains water-soluble CBD；
(5) the water-soluble CBD that will be obtained, is placed in spray dryer, and spray drying obtains water-soluble CBD product.
Due to the inedible property of rilanit special, the present embodiment selects soybean lecithin to carry out subsequent embedding.Through detecting, on
The water solubility for stating water solubility CBD product obtained is 15%.
Embodiment 3
Using CBD simple substance, single factor exploration carried out to the different amounts of gamma-cyclodextrin respectively, the unshowned raw material of table 1 with
And technological parameter is according to the raw material and technological parameter of embodiment two.
| CBD(kg) | Soybean lecithin (kg) | Gamma-cyclodextrin (kg) | Whipping temp (DEG C) | Mixing time (h) | |
| Scheme one | 1 | 14 | 0.3 | 50 | 3 |
| Scheme two | 1 | 14 | 0.9 | 50 | 3 |
| Scheme three | 1 | 14 | 1.8 | 50 | 3 |
| Scheme four | 1 | 14 | 3.6 | 50 | 3 |
| Scheme five | 1 | 14 | 7.2 | 50 | 3 |
Table 1
As a result as shown in Figure 2: with the increase of gamma-cyclodextrin dosage, CBD water solubility increases；When dosage reaches 1.8kg
When, CBD water solubility reaches maximum, and when being further continued for increasing the dosage of gamma-cyclodextrin, CBD water solubility is not further added by, or even has certain
It reduces.Therefore in specific operation, select cyclodextrin optimum amount for 1.8kg.
Embodiment 4
The present embodiment uses cyclodextrin mixed liquor, wherein the accounting for investigating gamma-cyclodextrin in mixed liquor is water-soluble to CBD
Influence, the unshowned raw material of table 2 and technological parameter according to embodiment two raw material and technological parameter.
Fig. 2
As a result as shown in Figure 3: with the increase of gamma-cyclodextrin and α, beta-cyclodextrin ratio, CBD water solubility is gradually reduced
Trend, when gamma-cyclodextrin and α, beta-cyclodextrin ratio are 1:4, CBD water solubility is larger, therefore it is subsequent to select this accounting to carry out
Experiment.
The dosage of 5 soybean lecithin of embodiment is to the water-soluble impact analysis of CBD
The present embodiment uses cyclodextrin mixed liquor, wherein investigating the dosage of soybean lecithin to the water-soluble influence of CBD, table 2
Unshowned raw material and technological parameter according to embodiment two raw material and technological parameter.
Table 3
As a result as shown in the figure: with the increase of soybean lecithin dosage, CBD water solubility increases；When dosage reaches 14kg,
CBD water solubility reaches maximum, and when being further continued for increasing the dosage of soybean lecithin, CBD water solubility is not further added by.Therefore selection CBD1kg
Corresponding soybean lecithin dosage is 14kg as calculating standard and carries out raw material addition.
6 whipping temp of embodiment and time are on the water-soluble influence of CBD:
Table 4 and table 5 are raw material and technological parameter under different whipping temps or mixing time, and unshowned use is implemented
The experimental data of example 2
Table 4
Table 5
As a result as shown in Figure 5: under conditions of determined above, when whipping temp is 50 DEG C, stirring 0.5h, CBD can be made
Solubility reaches optimum efficiency, and solubility can achieve 23% or so.
Claims (10)
1. a kind of preparation method of water solubility CBD, which is characterized in that this method comprises:
1) liphophilic solvents are dissolved in ethyl alcohol, form the first solution containing liphophilic solvents and ethyl alcohol；
2) CBD extract is dissolved in the first solution, and CBD association liquid is made；
3) CBD is associated into liquid and the second solution containing cyclodextrin mixes, and CBD is filled into cyclodextrin gap, made
Obtain the water-soluble CBD solution containing solvent；
4) solvent is removed, water-soluble CBD is obtained.
2. the preparation method of water solubility CBD according to claim 1, which is characterized in that the liphophilic solvents be containing
The phosphatide or phosphoglyceride of phosphoglyceride, rilanit special it is one or more.
3. the preparation method of water solubility CBD according to claim 2, which is characterized in that the cyclodextrin is α-ring paste
One or more of essence, beta-cyclodextrin, gamma-cyclodextrin.
4. the preparation method of water solubility CBD according to claim 3, which is characterized in that the ethyl alcohol that ethyl alcohol is 95%, oleophylic
Property solvent be dissolved in ethyl alcohol using electromagnetic heating blender, stirring rate 500r/min, 40-60 DEG C of heating temperature, mixing time
For 2-3h, mix, filtering.
5. the preparation method of water solubility CBD according to claim 4, which is characterized in that liphophilic solvents in the first solution
Mass ratio with ethyl alcohol is 1:10~1:20.
6. the preparation method of water solubility CBD according to claim 5, which is characterized in that CBD extract and the first solution
Mass ratio is 1:(40~200).
7. the preparation method of water solubility CBD according to claim 6, which is characterized in that include being added in step 2 by electromagnetism
The stirring of thermal agitation device, stirring rate 500r/min, 40-60 DEG C of heating temperature, the association time is 2-3h.
8. the preparation method of water solubility CBD according to claim 7, which is characterized in that step 4 includes following method: being set
In electromagnetic heating blender, stirring rate 500r/min 40-60 DEG C of heating temperature, stirs 2.5-3.5h, is uniformly mixed, mistake
Filter.
9. the preparation method of water solubility CBD according to claim 8, which is characterized in that in step 3 be added stabilizer with
CBD solution is inhibited sediment occur, stabilizer selects hydroxypropyl cellulose sodium, one kind of polyethylene glycol, polyvinylpyrrolidone
Or it is a variety of.
10. a kind of water solubility CBD, which is characterized in that prepared according to the described in any item methods of claim 1-9, the water
Dissolubility CBD includes liphophilic solvents, cyclodextrin.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021090003A1 (en) * | 2019-11-04 | 2021-05-14 | Grow Biotech Plc | Method for selective recovery of hydrophobic compounds |
| CN113244410A (en) * | 2021-05-28 | 2021-08-13 | 哈尔滨工业大学 | Preparation method of clathrate compound based on porous starch and used for increasing cannabidiol water solubility |
| WO2022238667A1 (en) * | 2021-05-13 | 2022-11-17 | Grow Group Plc | Method for selective recovery of lipophilic compounds |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050090468A1 (en) * | 2002-02-20 | 2005-04-28 | Tomi Jarvinen | Novel methylated cyclodextrin complexes |
| US20050153931A1 (en) * | 2002-02-20 | 2005-07-14 | Pedipharm Oy | Novel natural cyclodextrin complexes |
| CN101810660A (en) * | 2009-12-31 | 2010-08-25 | 江苏健佳药业有限公司 | Water-soluble silymarin and preparation method thereof |
| WO2017183011A1 (en) * | 2016-04-22 | 2017-10-26 | Degeeter David M | Water soluble cannabinoid inclusion complexes |
| CN109833312A (en) * | 2019-04-09 | 2019-06-04 | 栾云鹏 | A kind of cannabidiol and the inclusion compound of alkaline cyclodextrin and preparation method thereof |
-
2019
- 2019-07-02 CN CN201910590732.3A patent/CN110204426B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050090468A1 (en) * | 2002-02-20 | 2005-04-28 | Tomi Jarvinen | Novel methylated cyclodextrin complexes |
| US20050153931A1 (en) * | 2002-02-20 | 2005-07-14 | Pedipharm Oy | Novel natural cyclodextrin complexes |
| CN101810660A (en) * | 2009-12-31 | 2010-08-25 | 江苏健佳药业有限公司 | Water-soluble silymarin and preparation method thereof |
| WO2017183011A1 (en) * | 2016-04-22 | 2017-10-26 | Degeeter David M | Water soluble cannabinoid inclusion complexes |
| CN109833312A (en) * | 2019-04-09 | 2019-06-04 | 栾云鹏 | A kind of cannabidiol and the inclusion compound of alkaline cyclodextrin and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| JANNE MANNILA等: "Effects of RM-β-CD on sublingual bioavailability of Δ9-tetrahydrocannabinol in rabbits", 《EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES》 * |
| LV PIN等: "Structural analysis and cytotoxicity of host-guest inclusion complexes of cannabidiol with three native cyclodextrins", 《JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021090003A1 (en) * | 2019-11-04 | 2021-05-14 | Grow Biotech Plc | Method for selective recovery of hydrophobic compounds |
| CN114667155A (en) * | 2019-11-04 | 2022-06-24 | 成长生物科技有限公司 | Method for selectively recovering hydrophobic compound |
| WO2022238667A1 (en) * | 2021-05-13 | 2022-11-17 | Grow Group Plc | Method for selective recovery of lipophilic compounds |
| CN113244410A (en) * | 2021-05-28 | 2021-08-13 | 哈尔滨工业大学 | Preparation method of clathrate compound based on porous starch and used for increasing cannabidiol water solubility |
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Effective date of registration: 20230609 Address after: Room 401-195, Floor 4, Building 13, Harbin Songbei (Shenzhen Longgang) Science and Technology Innovation Industrial Park, No. 3043, Zhigu Second Street, Songbei District, Harbin, 150000 Patentee after: Heilongjiang Shenli Biotechnology Co.,Ltd. Address before: 1-302, back seat, 176 Xingang West Road, Xingang Street, Haizhu District, Guangzhou City, Guangdong Province, 510300 Patentee before: Liang Zhiquan |
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