Synthetic cannabidiol compositions and methods of making the same

Abstract

Disclosed herein are embodiments of a method for making cannabidiol. Also disclosed herein are embodiments of a composition comprising cannabidiol and one or more GRAS components. The method and composition embodiments described herein address the drawbacks associated with conventional methods for making and/or isolating cannabidiol.

We claim: 
     
         1 . A composition, comprising:
 cannabidiol; and   a terpene-containing component.   
     
     
         2 . The composition of  claim 1 , wherein the terpene-containing component is a Generally Recognized As Safe (“GRAS”) component. 
     
     
         3 . The composition of  claim 1 , wherein the terpene-containing component comprises orange terpenes, or valencene, or aristolochene, or limonene or any combination thereof. 
     
     
         4 . The composition of  claim 3 , wherein the limonene is D-limonene. 
     
     
         5 . The composition of  claim 1 , further comprising one or more Generally Recognized As Safe (“GRAS”) solvents selected from propylene glycol, or water, or glycerol, or ethanol, or any combination thereof. 
     
     
         6 . The composition of  claim 1 , wherein the cannabidiol is present in an amount ranging from greater than 50% to less than 100%. 
     
     
         7 . The composition of  claim 1 , wherein the composition is free of cannabidiol degradation products selected from Δ 9 -tetrahydrocannabinol; Δ 8 -tetrahydrocannabinol; dimers or trimers of cannabidiol; products formed by carbon-carbon bond formation between an olivetol molecule and two or more menthadienol molecules; regioisomeric products; steroisomeric byproducts; or oxidative degradation products. 
     
     
         8 . The composition of  claim 1 , comprising:
 cannabidiol; and   D-limonene, provided that the composition does not include a non-GRAS component, a cannabinoid other than cannabidiol, Δ 9 -tetrahydrocannabinol; Δ 8 -tetrahydrocannabinol; dimers or trimers of cannabidiol; products formed by carbon-carbon bond formation between an olivetol molecule and two or more menthadienol molecules, or other cannabidiol degradation products.   
     
     
         9 . A method for making synthetic cannabidiol, comprising:
 combining (+)-menthadienol and olivetol with a Lewis Acid catalyst to form a first reaction mixture comprising synthetic cannabidiol;   exposing the first reaction mixture to a terpene-containing component to form a second reaction mixture;   exposing the second reaction mixture to water to form an organic phase and an aqueous phase;   separating the organic phase from the aqueous phase; and   isolating the synthetic cannabidiol from the terpene-containing component.   
     
     
         10 . The method of  claim 9 , further comprising:
 performing a complexation procedure prior to isolating the synthetic cannabidiol from the terpene-containing component, comprising mixing the organic phase with an amine compound for a time sufficient to produce an insoluble complex comprising the amine and the synthetic cannabidiol; and wherein isolating the synthetic cannabidiol from the terpene-containing component comprises using filtration or centrifugation to isolate the insoluble complex.   
     
     
         11 . The method of  claim 9 , wherein the Lewis Acid catalyst is Zn(OTf) 2  or Sc(OTf) 3  and wherein the terpene-containing component is orange oil, orange terpenes, limonene, or a combination thereof. 
     
     
         12 . The method of  claim 9 , wherein the (+)-menthadienol and olivetol are mixed together and then the Lewis Acid catalyst is added. 
     
     
         13 . The method of  claim 9 , wherein the olivetol and the Lewis Acid catalyst are mixed together and then the (+)-menthadienol and is added. 
     
     
         14 . The method of  claim 9 , wherein the olivetol, the (+)-menthadienol, or both are diluted with a diluting solvent prior to combining the olivetol and the (+)-menthadienol. 
     
     
         15 . The method of  claim 14 , wherein the diluting solvent is selected from an aliphatic solvent, an aromatic solvent, or a halogenated solvent. 
     
     
         16 . The method of  claim 10 , further comprising (i) performing an aqueous alkaline wash procedure prior to performing the complexation procedure, the aqueous alkaline wash procedure comprising exposing the organic phase to an aqueous alkaline solution, mixing the organic phase with the aqueous alkaline solution, and filtering the organic phase to provide a clarified solution; (ii) washing the insoluble complex with a solvent; or (iii) a combination of (i) and (ii). 
     
     
         17 . The method of  claim 10 , wherein the amine compound is 1,4-diazabicyclo[2.2.2]octane, 1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione, nicotinamide, isonicotinamide, or 1,10-phenanthroline. 
     
     
         18 . The method of  claim 10 , wherein the complexation procedure further comprises drying the insoluble complex under vacuum and at a temperature ranging from 20° C. to 60° C. 
     
     
         19 . The method of  claim 10 , further comprising exposing the insoluble complex to a Generally Recognized As Safe (“GRAS”) solvent and an acid to convert the insoluble complex to free cannabidiol; and (i) treating the free cannabidiol with water to provide crystals of substantially pure cannabidiol; or (ii) forming a slurry comprising the free cannabidiol and a Generally Recognized As Safe (“GRAS”) solvent, and filtering and washing the slurry to provide crystals of substantially pure cannabidiol. 
     
     
         20 . An insoluble complex, comprising cannabidiol and 1,4-diazabicyclo[2.2.2]octane, 1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione, nicotinamide, isonicotinamide, or 1,10-phenanthroline, wherein the cannabidiol and the amine are present in a 1:1 ratio.