IP Library › Granted Patent US 12,484,606
Granted Patent B2
US 12,484,606 · App. 17/413,452 · Granted Dec 2, 2025

Compositions and methods related to anionic cannabinoid molecules

Inventor: Douglas G. Metcalf (Boulder, CO)
Assignee: Natural Extraction Systems, LLC
A23L33/105A23L2/38A23L2/52A23L2/60A23L29/035A61K31/658A61K36/185A23V2002/00A23V2250/2132
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Quick Facts
Patent No.
US 12,484,606
App. No.
17/413,452
Granted
Dec 2, 2025
Kind
B2
Abstract

This patent document discloses compositions and methods related to anionic cannabinoid molecules that contain oxide substituents.

Claims (33)

1 . A composition, comprising:

an anionic cannabinoid and a cannabinoid molecule at a molar ratio of 1:10 to 1,000,000:1; and

one or more of sodium ion (“Na + ”), potassium ion (“K + ”), calcium ion (“Ca 2+ ”), magnesium ion (“Mg 2+ ”), chloride ion (“Cl − ”), sulfate (“SO 4 2− ”), bicarbonate (“HCO 3− ”), and carbonate (“CO 3 2− ”);

wherein:

the anionic cannabinoid is (6aR,10aR)-3-alkyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

the anionic cannabinoid has a conjugate acid;

the conjugate acid is the cannabinoid molecule; and

the cannabinoid molecule is (6aR,10aR)-3-alkyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol.

2 . The composition of claim 1 , wherein the composition is a liquid, the composition has a pH, and the pH of the composition is 7 to 13.

3 . The composition of claim 1 , wherein the composition is a liquid, the composition has a pH, and the pH of the composition is 8 to 10.

4 . The composition of claim 1 , comprising the anionic cannabinoid and the cannabinoid molecule at a molar ratio of 1:10 to 10,000:1.

5 . The composition of claim 1 , comprising the anionic cannabinoid and the cannabinoid molecule at a molar ratio of 1:1 to 100:1.

6 . The composition of claim 1 , comprising water.

7 . The composition of claim 1 , comprising ethanol.

8 . The composition of claim 7 , comprising ethanol at a concentration by weight of 50 parts per million to 2 percent.

9 . The composition of claim 7 , comprising ethanol at a concentration by weight of 1 percent to 20 percent.

10 . The composition of claim 7 , comprising ethanol at a concentration by weight of 10 percent to 95 percent.

11 . The composition of claim 1 , comprising the anionic cannabinoid at a concentration of 1 milligram per liter to 100 milligrams per liter.

12 . The composition of claim 1 , comprising the anionic cannabinoid at a concentration of 50 milligrams per liter to 5 grams per liter.

13 . The composition of claim 1 , comprising the anionic cannabinoid at a concentration of 2 grams per liter to 200 grams per liter.

14 . The composition of claim 1 , wherein alkyl is selected from hydro, methyl, ethyl, prop-1-yl, but-1-yl, pent-1-yl, hex-1-yl, hept-1-yl, oct-1-yl, prop-2-yl, but-2-yl, pent-2-yl, hex-2-yl, hept-2-yl, oct-2-yl, 2-methylprop-2-yl, 2-methylbut-2-yl, 2-methylpent-2-yl, 2-methylhex-2-yl, 2-methylhept-2-yl, 2-methyloct-2-yl, 3-methylprop-2-yl, 3-methylbut-2-yl, 3-methylpent-2-yl, 3-methylhex-2-yl, 3-methylhept-2-yl, 3-methyloct-2-yl, and 2-phenyleth-1-yl.

15 . The composition of claim 1 , wherein alkyl is pent-1-yl.

16 . A composition, comprising an anionic cannabinoid and a cannabinoid molecule at a molar ratio of 1:10 to 10,000:1, wherein:

the anionic cannabinoid is (6aR,10aR)-3-alkyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

the anionic cannabinoid has a conjugate acid;

the conjugate acid is the cannabinoid molecule;

the cannabinoid molecule is (6aR,10aR)-3-alkyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol;

the composition comprises a solid phase;

the solid phase comprises a salt; and

the salt comprises the anionic cannabinoid.

17 . The composition of claim 16 , wherein the salt comprises a cation selected from sodium ion (Na + ), potassium ion (K + ), calcium ion (Ca 2+ ), and magnesium ion (Mg 2+ ).

18 . The composition of claim 16 , wherein alkyl is selected from hydro, methyl, ethyl, prop-1-yl, but-1-yl, pent-1-yl, hex-1-yl, hept-1-yl, oct-1-yl, prop-2-yl, but-2-yl, pent-2-yl, hex-2-yl, hept-2-yl, oct-2-yl, 2-methylprop-2-yl, 2-methylbut-2-yl, 2-methylpent-2-yl, 2-methylhex-2-yl, 2-methylhept-2-yl, 2-methyloct-2-yl, 3-methylprop-2-yl, 3-methylbut-2-yl, 3-methylpent-2-yl, 3-methylhex-2-yl, 3-methylhept-2-yl, 3-methyloct-2-yl, and 2-phenyleth-1-yl.

19 . The composition of claim 16 , wherein alkyl is pent-1-yl.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2025
From: METCALF, DOUGLAS G.
To: NATURAL EXTRACTION SYSTEMS, LLC
Reel/Frame 072758/0944 →
Continuity (17)
Continuation 16440878 · Jun 13, 2019
Continuation 16440889 · Jun 13, 2019
Continuation 16239463 · Jan 3, 2019
Provisional Application 62935484 · Nov 14, 2019
Provisional Application 62933748 · Nov 11, 2019
Provisional Application 62928941 · Oct 31, 2019
Provisional Application 62867207 · Jun 26, 2019
Provisional Application 62860223 · Jun 11, 2019
Provisional Application 62812845 · Mar 1, 2019
Provisional Application 62812849 · Mar 1, 2019
Provisional Application 62787717 · Jan 2, 2019
Provisional Application 62787722 · Jan 2, 2019
Provisional Application 62787720 · Jan 2, 2019
Provisional Application 62780178 · Dec 14, 2018
Provisional Application 62780169 · Dec 14, 2018
Provisional Application 62780176 · Dec 14, 2018
Related Publication 20220071256A1 · Mar 10, 2022
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