Methods of producing anionic cannabinoid molecules dissolved in water
Various aspects of this patent document relate to methods to produce compositions comprising anionic cannabinoid molecules.
1. A method to solubilize a cannabinoid in water, comprising:
providing a cannabinoid molecule, the cannabinoid molecule is cannabidiol and comprises an aromatic ring and a hydroxyl group, and the hydroxyl group is a substituent on the aromatic ring;
providing a Brønsted base and ethanol;
providing water;
contacting the cannabinoid molecule with the Brønsted base and the ethanol to deprotonate the hydroxyl group and to produce an anionic cannabinoid molecule; and
dissolving the anionic cannabinoid molecule in the water to produce a solution comprising the anionic cannabinoid molecule;
the solution comprising the anionic cannabinoid molecule has a pH of at least 8.5; and the anionic cannabinoid molecule is selected from the group consisting of:
2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate; 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-3-hydroxy-5-pentylphenolate; 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentyl-1,4-benzoquinone-3-oxide;
3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-6-pentyl-1,2-benzoquinone-4-oxide;
2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-5-pentyl-1,4-benzoquinone-3-oxide;
3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-6-pentyl-1,2-benzoquinone-4-oxide; and
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-oxide.
2. The method of claim 1 , in which the cannabinoid molecule is cannabidiol, and the anionic cannabinoid molecule is 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate.
3. The method of claim 1 , in which the Brønsted base is ethoxide or hydroxide.
4. The method of claim 1 , which either (i) the cannabinoid molecule, (ii) the Brønsted base, or (iii) both the cannabinoid molecule and the Brønsted base are dissolved in a solvent when the cannabinoid molecule and the Brønsted base are contacted with each other.
5. The method of claim 4 , in which the solvent is ethanol.
6. The method of claim 5 , which the solution has an ethanol concentration, and the method comprises adjusting the ethanol concentration of the solution to an ethanol concentration no greater than 0.05% by weight.
7. The method of claim 4 , in which the solvent has a dissolved oxygen concentration, and the method comprises reducing the dissolved oxygen concentration of the solvent prior to contacting the cannabinoid molecule with the Brønsted base.
8. The method of claim 1 , which the water has a dissolved oxygen concentration, and the method comprises reducing the dissolved oxygen concentration of the water prior to dissolving the anionic cannabinoid molecule in the water.
9. The method of claim 1 , in which the water has a pH, and the pH is greater than 9.5.
10. The method of claim 1 , in which the solution comprising the anionic cannabinoid molecule has a pH, and the method comprises adjusting the pH to 8.5 to 10.5.
11. The method of claim 1 , comprising adjusting a concentration of the anionic cannabinoid molecule in the solution to a concentration of 20 micrograms per liter to 2000 milligrams per liter.
12. The method of claim 1 , in which the method results in a lipid phase in fluid communication with the solution comprising the anionic cannabinoid molecule, and the method comprises separating the lipid phase from the solution.
13. The method of claim 1 , comprising inserting the solution comprising the anionic cannabinoid molecule into a container and then hermetically-sealing the container.
14. The method of claim 13 , comprising inserting 25 milliliters to 800 milliliters of the solution into the container.
15. The method of claim 13 , comprising transferring ownership of the container and receiving payment for transferring ownership of the container.
16. The method of claim 1 , in which:
the cannabinoid molecule is cannabidiol;
the anionic cannabinoid molecule is 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate;
the Brønsted base is dissolved in a solvent when the cannabinoid molecule and the Brønsted base are contacted with each other;
the solvent is ethanol;
the Brønsted base is hydroxide or ethoxide;
the water has a pH;
the pH of the water is greater than 9.5;
the solution comprising the anionic cannabinoid molecule has a pH;
either the pH of the solution is 8.5 to 10.5, or the method comprises adjusting the pH of the solution to 8.5 to 10.5; and
the method comprises inserting the solution comprising the anionic cannabinoid molecule into a container and then hermetically-sealing the container.