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Cannabidiol-3-sulfonic acid, preparation method and application thereof, and cannabidiol derivative

A technology of cannabidiol and derivatives, which is applied in the field of medicine and chemical industry to achieve the effects of increasing water solubility, increasing medicinal properties and improving water solubility

Active Publication Date: 2021-03-05
析木津生物医药(广州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The ester solubility of CBD makes it very limited in drug development

Method used

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  • Cannabidiol-3-sulfonic acid, preparation method and application thereof, and cannabidiol derivative
  • Cannabidiol-3-sulfonic acid, preparation method and application thereof, and cannabidiol derivative
  • Cannabidiol-3-sulfonic acid, preparation method and application thereof, and cannabidiol derivative

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preparation example Construction

[0032] The present invention provides the preparation method of cannabidiol-3-sulfonic acid described in the above technical scheme, comprising the following steps:

[0033] Mix cannabidiol with concentrated sulfuric acid for sulfonation reaction to obtain cannabidiol-3-sulfonic acid.

[0034] In the present invention, unless otherwise specified, the required preparation materials are commercially available products well known to those skilled in the art.

[0035] The invention mixes cannabidiol and concentrated sulfuric acid to carry out sulfonation reaction to obtain cannabidiol-3-sulfonic acid. In the present invention, the concentrated sulfuric acid is preferably commercially available concentrated sulfuric acid, that is, concentrated sulfuric acid with a mass fraction of 98%.

[0036] In the present invention, the molar ratio of cannabidiol to concentrated sulfuric acid is preferably 1:15-30, more preferably 1:20-25. In the present invention, the mixing process is prefe...

Embodiment 1

[0055] The ratio of cannabidiol to concentrated sulfuric acid molar ratio is 1:15 to react.

[0056] Weigh 50g of concentrated sulfuric acid and add it to a three-necked flask, cool it down to 0°C naturally in an ice-water bath, add 10.68g of cannabidiol, control the temperature below 20°C, after the addition is complete, then control the temperature at 20°C, carry out the sulfonation reaction for 4 hours, and stop the reaction. Pour the resulting reaction liquid into an ice-water bath, and carry out ethyl acetate extraction. The extracted organic phase was concentrated under reduced pressure at 50°C and then placed on a 200-300 mesh silica gel column. =8:1:1) to elute 2 column volumes, then change to eluent 2 (petroleum ether:ethyl acetate:methanol=4:1:2) to elute 3 column volumes, collect eluent 2 to wash Partially removed, after drying under reduced pressure, add an appropriate amount of methanol at room temperature until the solids are completely dissolved, let stand at ro...

Embodiment 2

[0060] The reaction is carried out in a ratio of 1:30 by the molar ratio of cannabidiol and concentrated sulfuric acid.

[0061] Weigh 50g of concentrated sulfuric acid and add it to a three-necked flask, cool it down to 0°C naturally in an ice-water bath, add 5.34g of cannabidiol, control the temperature below 15°C, after the addition is complete, then control the temperature at 25°C, carry out the sulfonation reaction for 2 hours, and stop the reaction. Pour the resulting reaction solution into an ice-water bath, extract with ethyl acetate, dry the extracted organic phase under reduced pressure at 50°C, dissolve it in 10% ethanol solution, and load it on an AB-8 macroporous adsorption resin column , first wash 5 column volumes with 10% ethanol, then wash 3 column volumes with 50% ethanol, and finally wash the column with 3 column volumes of 95% ethanol; collect 50% ethanol eluted parts, dry under reduced pressure Add an appropriate amount of absolute ethanol until the solid ...

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Abstract

The invention belongs to the technical field of pharmaceutical chemicals, and particularly relates to cannabidiol 3sulfonic acid, a preparation method and application thereof, and a cannabidiol derivative. According to the invention, a sulfonic acid group is introduced into the molecular structure of cannabidiol, the sulfonic acid group used as a polar group can increase the polarity of the cannabidiol so as to improve the water solubility of the cannabidiol, the cannabidiol-3-sulfonic acid can be subjected to salt forming reaction with inorganic base or organic base, the water solubility of the cannabidiol is further increased, and the druggability of a medicine based on the CBD structure parent nucleus and the physiological activity can be improved; and besides, on the premise of ensuring that the basic structure parent nucleus of the cannabidiol is not greatly changed, the sulfonic group newly introduced into the cannabidiol-3-sulfonic acid provided by the invention can be used as anew action site to react with a specific group, thereby further widening the research and application range of the cannabidiol-3-sulfonic acid.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a cannabidiol derivative, a preparation method and application thereof, and a cannabidiol derivative. Background technique [0002] Cannabidiol (CBD), alias L-trans-cannabidiol; English name (-)-cannabidiol; Chinese chemical name is 2-[(1R, 6R)-3-methyl-6-(1 -Methylvinyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol; English chemical name: 2-[(1R,6R)-3-methyl-6- (1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzonediol; molecular formula: C 21 h 30 o 2 ; Molecular Weight: 314.46; CAS Registry Number: 13956-29-1. [0003] [0004] Cannabidiol (CBD) is one of the main phenolic chemical components in cannabis. In vivo experiments have found that CBD can not only antagonize the psychoactive effect of THC on the cannabinoid type I receptor (CB1R), but also has anticonvulsant, sedative-hypnotic, It has anti-anxiety, anti-psychotic, anti-inflammatory an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/42C07C303/06C07C303/44C07C303/32C07C303/38C07C311/29C07C309/87C07C303/02
CPCC07C303/02C07C303/06C07C303/32C07C303/38C07C303/44C07C309/42C07C309/87C07C311/29C07C2601/16B01D15/265B01D15/34C07B2200/07B01D15/08
Inventor 曲桂武崔明
Owner 析木津生物医药(广州)有限公司
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