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Cannabidiol cyclodextrin conjugate and preparation method thereof

A technology of cannabidiol cyclodextrin and cannabidiol, which is applied in the directions of active ingredients of hydroxyl compounds, pharmaceutical formulations, food science, etc., can solve problems such as restricting cannabidiol, and achieve higher stability, high yield and water solubility. Good results

Active Publication Date: 2020-12-22
云南佩林科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the fact that cannabidiol is almost insoluble in water and seriously restricts the application of cannabidiol, the present invention introduces amino cyclodextrin groups through covalent bonds to improve the water solubility of cannabidiol, and provides a class of cannabidiol with better water solubility, Cannabidiol aminocyclodextrin conjugate with excellent stability and no toxic side effects

Method used

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  • Cannabidiol cyclodextrin conjugate and preparation method thereof
  • Cannabidiol cyclodextrin conjugate and preparation method thereof
  • Cannabidiol cyclodextrin conjugate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]Example 1: The structural formula of the cannabidiol cyclodextrin conjugate in this example is as follows:

[0041]

[0042] The preparation method of above-mentioned cannabidiol cyclodextrin conjugate is as follows:

[0043] 1. Preparation of cannabidiol succinic acid derivatives

[0044] Dissolve 1g of cannabidiol in 10mL of chloroform, then add 3.6mg of DMAP, 296mg of succinic anhydride, and 145μL of ethylenediamine, stir and react at 100°C for 0.1h, extract with ethyl acetate, wash with saturated saline, and water After washing, the organic layer was dried with anhydrous sodium sulfate, filtered, and spin-dried to obtain a crude product; the crude product was then passed through a silica gel column, eluted with a dichloromethane-methanol mixture (volume ratio 20:1), and the eluate was collected and spin-dried The obtained carboxylic acid derivatized cannabidiol;

[0045]

[0046] NMR detection such as figure 1 , 2 , 4, there is an ethyl peak at 2.6-2.9ppm, ...

Embodiment 2

[0058] Example 2: The structural formula of the cannabidiol cyclodextrin conjugate in this example is as follows:

[0059]

[0060] The preparation method of above-mentioned cannabidiol cyclodextrin conjugate is as follows:

[0061] 1, the preparation method of cannabidiol succinic acid derivative is the same as embodiment 1 step 1;

[0062] 2. Preparation of mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin

[0063] Reference [B.L.May, S.D.Kean, C.J.Easton, and S.F.Lincoln: J.Chem.Soc., Perkin Trans.13157–3160 (1997)]; take single 6-p-toluenesulfonyl-β-cyclodextrin (3g , 2.329mmol) into 20mL of anhydrous diethylenetriamine solution, add Molecular sieves were reacted at 80°C for 12 hours. After the reaction was completed, the molecular sieves were removed by filtration, and then the clear solution was added dropwise to acetone, stirred for 30 minutes, and a white precipitate was obtained by suction filtration, dried in vacuum for 24 hours, and then dissolved with 5-10...

Embodiment 3

[0067] Embodiment 3: The structural formula of the cannabidiol cyclodextrin conjugate in this embodiment is as follows:

[0068]

[0069] The preparation method of above-mentioned cannabidiol cyclodextrin conjugate is as follows:

[0070] 1, the preparation method of cannabidiol succinic acid derivative is the same as embodiment 1 step 1;

[0071] 2. Preparation of mono-[6-(amino)-6-deoxy]-β-cyclodextrin

[0072] Dissolve mono-6-p-toluenesulfonyl-β-cyclodextrin (3.25g, 2.5mmol) and sodium azide (0.2g, 3.075mmol) in 25mL of DMF, N 2 Protected and reacted at 80°C for 12h. After cooling to room temperature, the N 2 Protected, filtered to obtain a yellow filtrate, and then the filtrate was dropped into acetone for recrystallization; the above operation was repeated until there was no impurity, and the product was dried in vacuum to obtain 2.6g, with a yield of 86%;

[0073] Add mono-6-azido-β-cyclodextrin (2.0g, 1.76mmol) into 10mL of DMF, then add triphenylphosphine (2.27g...

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Abstract

The invention discloses a cannabidiol cyclodextrin conjugate and a preparation method thereof. The conjugate disclosed by the invention is prepared by carrying out an amidation reaction on carboxylicacid derivatized cannabidiol and amino modified cyclodextrin in an organic solvent under the action of an alkali and a condensing agent. According to the invention, compared with cannabidiol, the cannabidiol cyclodextrin conjugate disclosed by the invention has more hydrophilic active groups, good biocompatibility and better water solubility; and the preparation method of the cannabidiol cyclodextrin conjugate is simple, raw materials are easy to obtain, reaction conditions are mild, and the cannabidiol cyclodextrin conjugate is suitable for industrial production and market popularization andapplication.

Description

technical field [0001] The invention belongs to the field of medicine, food and health product preparation, and in particular relates to a class of cannabidiol cyclodextrin conjugates and a preparation method thereof. Background technique [0002] Cannabidiol (CBD) is a pure natural ingredient extracted from the cannabis plant. It is generally a white or light yellow resin or crystal, with a melting point of 66°C-67°C, and is almost insoluble in water. Cannabidiol can block the adverse effects of certain polyphenols on the human nervous system, and can block breast cancer metastasis, relieve pain, treat epilepsy, anti-rheumatoid arthritis, anti-spasm, anti-insomnia, anti-anxiety, antibacterial and anti-inflammatory, etc. Physiological functions; In addition, recent studies have found that cannabidiol also has great application potential in food, health products, cosmetics and other fields. [0003] However, cannabidiol is almost insoluble in water and easily decomposed when...

Claims

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Application Information

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IPC IPC(8): C08B37/16A23L29/30A23L33/105A61K31/05A61K47/69
CPCC08B37/0012A61K31/05A61K47/6951A23L33/105A23L29/35A23V2002/00A23V2250/2132A23V2250/5112
Inventor 杨蕾杨波王海琨王静廖霞俐李字明李婷
Owner 云南佩林科技有限公司
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