US 2024/0190834 A1 · METHODS FOR EXTRACTION, PROCESSING, AND PURIFICATION OF MINOR CANNABINOID COMPOUNDS FROM COMPLEX MIXTURES

Abstract

Disclosed are methods for separating, recovering, and purifying CBGA, CBDVA, THCVA, CBCVA, and CBCA from dewatered and desolventized crude complex extracts or mixtures of metabolites, cannabinoids, and Cannabis phytochemicals. The methods comprise solubilizing the extracts or mixtures of cannabinoids in a selected solvent, adding a selected amine to precipitate a CBGA-amine or CBDVA-amine or THCVA-amine or CBCVA-amine or CBCA-amine salt therefrom, dissolving the recovered amine salt in a selected solvent, and adding a selected antisolvent to recrystallize a purified amine salt therefrom. The recrystallized amine salt may be decarboxylated to form a mixture of CBG or CBDV or THCV or CBCV or CBC and amine. The cannabinoid and amine mixture may be acidified to separate the amine from CBG or CBDV or THCV or CBCV or CBC. The recovered CBG or CBDV or THCV or CBCV or CBC may then be concentrated.

Claims20

Dependent claims

1-99. (canceled)

A method for separating, recovering, and purifying a cannabigerolic acid-amine salt (CBGA-amine salt) or a Δ9-tetrahydrocannabivaric acid-amine salt (THCVA-amine salt) or a cannabidivarinic acid-amine salt (CBDVA-amine salt) or a cannabichromevarinic acid-amine salt (CBCVA-amine salt) or a cannabichromenic acid-amine salt (CBCA-amine salt from an organic solvent solution comprising a mixture of cannabinoids, said method comprising:

(i) providing a crude complex extract or mixture containing therein a complex mixture of metabolites and cannabinoids recovered from a Cannabis biomass or from cultured microbial fermentation systems, with an extractant solvent selected from one of methanol, ethanol, propanol, isopropanol, butanol, heptane, hexane, propane, butane, ethyl acetate, acetone, dichloromethane, 1,4-dioxane, tetrahydrofuran, acetonitrile, toluene, methyl tert-butyl ether, supercritical CO2, subcritical CO2, or recovered by microfiltration;
(ii) removing the extractant solvent from the crude extract or mixture and drying the desolventized crude extract or mixture to thereby produce a concentrated complex extract;
(iii) assaying the concentrated crude extract or mixture to determine a first concentration of CBGA or THCVA or CBDVA or CBCVA or CBCA therein;
(iv) adding a volume of a first organic solvent selected from ethyl acetate, ethanol, isopropanol, propanol, butanol, hexane, heptane and dichloromethane, to the concentrated crude extract and commingling therewith to adjust the first CBGA or THCVA or CBDVA or CBCVA or CBCA concentration to a target concentration value selected from a range of target concentrations, thereby producing a solvent-solubilized complex extract solution or complex mixture solution;
(v) adding a selected amine to the solvent-solubilized complex extract solution or complex mixture solution, and commingling therewith to precipitate therefrom a CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt;
(vi) washing the precipitated CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt at least once with said first organic solvent and then drying the washed CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt;
(vii) dissolving the washed and dried CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt in a second organic solvent selected from ethanol, denatured ethanol, ethyl acetate, and dichloromethane, and commingling therewith;
(viii) adding a volume of an antisolvent selected from pentane, hexane, heptane, petroleum ethers, and water, to the dissolved CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt and commingling therewith to thereby recrystallize the CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt;
and
(ix) washing the recrystallized CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt at least once with said selected antisolvent to produce a purified CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt, and then drying the purified CBGA-amine salt or THCVA-amine salt or CBDVA-amine salt or CBCVA-amine salt or CBCA-amine salt.

7 more elements

Dependencies are inferred from the claim text.

Methods for extraction, processing, and purification of minor cannabinoid compounds from complex mixtures

Life of this patent

Methods for extraction, processing, and purification of minor cannabinoid compounds from complex mixtures

Life of this patent

Abstract

Claims20