Cannabidiol compositions having modified cannabinoid profiles
AssigneePurisys LLC
InventorsDaniel M. Hallow, Jun He, Mark C. Dobish, Denis Petrovic, Gnel Mkrtchyan
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Abstract
The present disclosure relates to the preparation of a highly pure cannabidiol compound by a novel synthesis route. The cannabidiol compound can be prepared by an acid-catalyzed reaction of a di-halo olivetol with menthadienol, followed by two crystallization steps. The highly pure cannabidiol compound is produced in high yield, stereospecificity, or both, and shows exceedingly low levels of Δ-9-tetrahydrocannabinol at the time of preparation and after storage.
Claims20
A composition comprising cannabidiol and delta-9-tetrahydrocannabinol, wherein said delta-9-tetrahydrocannabinol is present in an amount less than 10 ppm.
A stable composition comprising cannabidiol and delta-9-tetrahydrocannabinol, wherein said delta-9-tetrahydrocannabinol is present in an amount less than 10 ppm upon storage for 2 years or less.
A composition comprising cannabidiol and less than 10 ppm delta-9-tetrahydrocannabinol, wherein the ratio of cannabidiol to delta-9-tetrahydrocannabinol is less than 1:0.0001 as measured by UPLC.
A formulation comprising,
- cannabidiol,
- delta-9-tetrahydrocannabinol, wherein said delta-9-tetrahydrocannabinol is present in an amount less than 10 ppm, and
- a pharmaceutically acceptable excipient.
A method of preparing a cannabidiol composition, comprising
- contacting di-halo olivetol with menthadienol in the presence of a protic acid catalyst to prepare di-halo cannabidiol;
- contacting the di-halo cannabidiol with a reducing agent to prepare a first cannabidiol composition;
- contacting the first cannabidiol composition with a first solvent;
- crystallizing a second cannabidiol composition from said solvent;
- and
- recrystallizing crystalline cannabidiol composition having less than 10 ppm delta-9-tetrahydrocannabinol from a second solvent.
A method of recrystallizing cannabidiol from a mixture of cannabinoids to prepare a composition comprising cannabidiol and less than 10 ppm delta-9-tetrahydrocannabinol, said method comprising,
- contacting said mixture of cannabinoids with isooctane to form a solution;
- heating said solution to about 40° C.;
- cooling the solution to about 32° C.;
- seeding said solution at about 32° C. with (−)-Cannabidiol to prepare a suspension;
- allowing said suspension to warm to about 32° C. with stirring;
- cooling the suspension to −20° C.;
- separating a solid material from said suspension;
- washing solid material with isooctane at about −20° C.;
- and
- drying the solid material to obtain a crystalline composition comprising cannabidiol and less than 10 ppm delta-9-tetrahydrocannabinol.
Dependencies are inferred from the claim text.