CANNABICITRAN COMPOSITIONS AND METHODS OF SYNTHESIZING CANNABICITRAN
Compositions having enhanced cannabicitran concentrations and/or enhanced cannabicitran-derivative concentrations are disclosed herein as are methods of synthesizing cannabicitran and/or cannabicitran derivatives. Relative to conventional methods, the methods of the present disclosure may: (i) be better suited to large-scale conditions in that they do not require dangerous and/or toxic solvents and/or reagents; (ii) be more tolerant of complex starting compositions, such as cannabinoid isolates and/or distillates; (iii) provide cannabicitran and/or cannabicitran derivatives at higher yield; (iv) provide easier to purify product mixtures comprising cannabicitran and/or cannabicitran derivatives; (v) provide product mixtures comprising cannabicitran or cannabicitran derivatives that are easier to purify; (vi) provide product mixtures that comprise unique ratios of cannabicitran or cannabicitran derivatives relative to other cannabinoids; and/or (vii) provide product mixtures with reduced THC concentrations.
1 . A method of converting cannabichromene (CBC) or a CBC derivative to cannabicitran or a cannabicitran derivative, the method comprising heating the CBC or the CBC derivative at a pressure below about 1 bar and in the absence of a solvent.
2 .- 5 . (canceled)
6 . The method of claim 1 , wherein the heating is at a temperature between about 100° C. and about 150° C.
7 . The method of claim 6 , wherein the temperature is between about 120° C. and about 130° C.
8 . The method of claim 1 , wherein the heating is at a temperature between about 150° C. and about 220° C.
9 . The method of claim 8 , wherein the temperature is between about 190° C. and about 210° C.
10 .- 13 . (canceled)
14 . The method of claim 1 , wherein the CBC derivative is of the form:
and
the cannabicitran derivative is of the form:
wherein R is methyl, ethyl, propyl, butyl, heptyl, 1,1-dimethylheptyl, phenylethyl, phenylvinyl, or benzofuran.
15 .- 25 . (canceled)
26 . A method of preparing cannabicitran or a cannabicitran derivative, the method comprising:
heating a reaction mixture comprising citral, a modified resorcinol, and an amine under a first set of reaction conditions to form a first product mixture; and
heating at least a portion of the first product mixture, under a second set of reaction conditions to form cannabicitran or cannabicitran derivative.
27 . The method of claim 26 , wherein the second set of reaction conditions comprises a pressure below about 1 bar.
28 . (canceled)
29 . The method of claim 26 , wherein the second set of reaction conditions comprises a pressure at about 1 bar.
30 . The method of claim 26 , wherein the second set of reaction conditions is in the absence of a solvent.
31 . The method of claim 26 , wherein the second set of reaction conditions comprises a temperature between about 100° C. and about 150° C.
32 . The method of claim 31 , wherein the second temperature is between about 120° C. and about 130° C.
33 . The method of claim 26 , wherein the second set of reaction conditions comprises a temperature between about 150° C. and about 220° C.
34 . (canceled)
35 .- 38 . (canceled)
39 . The method of claim 26 , wherein the modified resorcinol is of the form:
40 . The method of claim 26 , wherein the modified resorcinol is of the form:
and
the cannabicitran derivative is of the form:
wherein R is methyl, ethyl, propyl, butyl, heptyl, 1,1-dimethylheptyl, phenylethyl, phenylvinyl, or benzofuran.
41 .- 44 . (canceled)
45 . The method of claim 26 , wherein the amine comprises a primary amine, a secondary amine, a tertiary amine, or a combination thereof.
46 . The method of claim 26 , wherein the amine comprises a class 3 solvent, a natural amine, or a combination thereof.
47 . The method of claim 26 , wherein the first set of reaction conditions comprise contacting the citral, the modified resorcinol, and the amine with a class 3 solvent.
48 .- 94 . (canceled)
95 . A method of converting cannabichromene (CBC) or a CBC derivative to cannabicitran or a cannabicitran derivative, the method comprising heating the CBC or the CBC derivative at a temperature between 100° C. and 150° C., at atmospheric pressure, and for a time of at least 8 hours.
96 . The method of claim 95 , wherein the CBC derivative is of the form:
and
the cannabicitran derivative is of the form:
wherein R is methyl, ethyl, propyl, butyl, heptyl, 1,1-dimethylheptyl, phenylethyl, phenylvinyl, or benzofuran.