Compositions and methods related to dissolved oxides
Various aspects of this patent document relate to compositions that comprise an anion that is the conjugate base of a hydrophobic molecule that has a pKa, for example, of at least 7 and no greater than 12. These compositions display improved properties when formulated to interact with an organism because the anions carry negative charges that allows them to both dissolve in water-miscible liquids and maximize their surface area. Interaction with an organism results in at least partial conversion of the anion into the hydrophobic molecule after which the hydrophobic molecule partitions out of a water-miscible liquid and into the organism.
1. A composition comprising a liquid phase that comprises a potassium cation, an anion and a solvent, and further comprises ethanol, wherein:
the solvent is at a concentration of at least 50 percent by mass;
the solvent is propane-1,2,3-triol;
the anion is dissolved in the solvent;
the anion has a net charge of −1;
the anion has a conjugate acid that is a molecule;
the molecule has a net charge of zero;
the molecule has a solubility in water that is less than 10 grams per liter at a pH of 7;
the molecule comprises a hydroxyl group that comprises an oxygen atom that is covalently bound to a carbon atom of an aromatic ring of the molecule by a single bond;
the anion comprises exactly one oxide group, and the oxide group comprises an oxygen atom that is covalently bound to a carbon atom of an aromatic ring of the anion by a single bond;
the oxygen atom of the hydroxyl group of the molecule has a connectivity to other heavy atoms of the molecule;
the oxygen atom of the oxide group of the anion has a connectivity to other heavy atoms of the anion; and
the connectivity of the oxygen atom of the hydroxyl group of the molecule to other heavy atoms of the molecule is identical to the connectivity of the oxygen atom of the oxide group of the anion to other heavy atoms of the anion;
the anion has a general formula I;
each skeletal atom of general formula I is a carbon atom;
the dotted lines represent aromaticity;
R1† is oxide; R3 is 6-(prop-1-en-2-yl)-3-methyl-cyclohex-2-en-1-yl; R5t is hydroxy; R7 is H; R11 is H; and
R9 is selected from an unsubstituted C3-C10 cycloalkyl; and a substituted or unsubstituted, straight or branched C1-12 alkyl; wherein substitution refers to at least one of:
(i) the substitution of two hydrogen atoms with a double bond;
(ii) the substitution of a hydrogen atom with an unsubstituted straight C1-C12 alkyl; and
(iii) the substitution of two hydrogen atoms with methylene or an unsubstituted, straight C1-C12 alkyl such that the substitution of the two hydrogen atoms forms a cycle that consists of 3 to 14 atoms; and
R9 is selected such that the anion comprises (i) at least 6 and no greater than 45 carbon atoms, (ii) at least 5 and no greater than 60 hydrogen atoms, and (iii) at least 1 and no greater than 12 oxygen atoms.
2. The composition of claim 1 , comprising water.
3. The composition of claim 1 , comprising the cation and the anion at a molar ratio of at least 1:1 and no greater than 5:4.
4. The composition of claim 1 , comprising a concentration of the anion that is dissolved in the solvent, wherein the molecule has a solubility in the liquid phase at a neutral pH that is less than the concentration of the anion that is dissolved in the solvent.
5. The composition of claim 1 , comprising the molecule and the anion at a molar ratio of at least 1:1,000,000 and less than 10:1.
6. The composition of claim 1 , comprising the anion at a concentration of at least 1 gram per liter.
7. The composition of claim 1 , wherein R9 is selected from methyl; ethyl; propyl; butyl; pentyl; hexyl; heptyl; ethenyl; prop-1-enyl; propen-2-yl; isoprenyl; geranyl; and a methyl, ethyl, propyl, butyl, pentyl, hexyl or heptyl that is substituted with 1, 2, or 3 groups selected from methyl, ethyl, and propyl.
8. The composition of claim 1 , wherein the anion is selected from
3-hydroxy-2-[(1R,6R)-6-(prop-1-en-2-yl)-3-methyl-cyclohex-2-en-1-yl]-5-pentyl-benzene-1-oxide;
3-hydroxy-2-[(1R,6R)-6-(prop-1-en-2-yl)-3-methyl-cyclohex-2-en-1-yl]-5-propyl-benzene-1-oxide;
3-hydroxy-2-[(1R,6R)-6-(prop-1-en-2-yl)-3-methyl-cyclohex-2-en-1-yl]-5-heptyl-benzene-1-oxide; and
3-hydroxy-2-[(1R,6R)-6-(prop-1-en-2-yl)-3-methyl-cyclohex-2-en-1-yl]-5-(2-methyl-octan-2-yl)-benzene-1-oxide.
9. The composition of claim 1 , wherein the anion is 3-hydroxy-2-[(1R,6R)-6-(prop-1-en-2-yl)-3-methyl-cyclohex-2-en-1-yl]-5-pentyl-benzene-1-oxide.
10. A method to produce a composition according to claim 1 , comprising:
combining the molecule, a strong Brønsted base comprising potassium, and an initial alcohol comprising ethanol to produce a first composition that comprises the anion, wherein the anion is dissolved in the initial alcohol;
providing a second composition that comprises propane-1,2,3-triol as solvent; and
combining the first composition and the second composition to dissolve the anion in the solvent and produce the composition of claim 1 .