CPC DISTRIBUTION CHROMATOGRAPHY OF CANNABINOIDS

Abstract

The invention relates to cannabinoids and their isolation and purification and to obtaining them by means of centrifugal partition chromatography.

Claims

1.-11. (canceled)

12. A method for separating and/or purifying cannabinoids from a cannabis extract, including at least one liquid-liquid centrifugal partition chromatography step, wherein a solvent from the group of cyclohexane, heptane, or octane is selected and is kept stationary by centrifugal force, including and a second non-miscible liquid phase.

13. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, wherein the first phase is n-heptane.

14. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, wherein the second phase is acetonitrile, methanol, ethylacetate or water.

15. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, selected from the group consisting of: n-heptane/acetonitrile, n-heptane/ethylacetate/acetonitrile, n-heptane/ethylacetate/t-butyl methyl ether/acetonitrile, n-heptane/ethylacetate/methanol/water, n-heptane/methanol/water, n-heptane/ethanol/water, n-heptane/acetone/water, n-heptane/methanol/acetonitrile, n-heptane/ethanol/acetonitrile, n-heptane/acetone/acetonitrile, n-heptane/chloroform/acetonitrile, n-heptane/chloroform/methanol, n-heptane/methanol, n-heptane/ethanol/methanol, n-heptane/n-butanol/acetonitrile, n-heptane/2-propanol/water, n-heptane/n-propanol/water, n-heptane/2-propanol/acetonitrile, n-heptane/n-propanol/acetonitrile, n-heptane/dichloromethane/acetonitrile, n-heptane/dichloromethane/methanol, n-heptane/tetrahydrofuran/acetonitrile, n-heptane/benzotrifluoride/acetonitrile, Cyclohexane/methanol/water, Cyclohexane/methanol/acetonitrile, Cyclohexane/t-butyl methyl ether/water, Cyclohexane/acetonitrile/water, and Isooctane/methanol, isooctane/methanol/water, Isooctane/ethyl acetate/methanol/water.

16. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, wherein 1 to 15% (v/v), 9 to 13% (v/v) t-butyl methyl ether is added to cyclohexane, heptane, or octane and/or the second non-miscible liquid.

17. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, having a flow of 50 to 600 mL per min. and/or a speed of 50 to 1,500 rpm.

18. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, wherein the two phases are conducted in the counter current and continuous separation occurs.

19. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, wherein at least one preparative column is upstream or downstream.

20. A cannabis extract obtainable according to a method from claim 12, wherein the dronabinol purity is greater than 95%.

21. A cannabis extract obtainable according to a method from claim 12, wherein the dronabinol purity is 99.6%.

22. A cannabis extract obtainable according to a method from claim 12, wherein the cannabidiol purity is greater than 95%.

23. A cannabis extract obtainable according to a method from claim 12, wherein the cannabidiol purity is 99.3%.

24. The method for separating and/or purifying cannabinoids from a cannabis extract according to claim 12, wherein a centrifugal partition chromatograph for separating and/or purifying cannabinoids is used.

Description

EXAMPLE AND FIGURES

[0076] These examples and figures are intended solely for explaining the invention, without limiting the invention to these examples.

Example 1

Cannabinoids from Hemp

[0077] Recovery of THC (dronabinol) (FIGS. 1-7), CED (FIG. 8), or CBC (FIG. 9) from pharmaceutical hemp or industrial/fiber hemp: extraction of cannabis flos by means of heptane, decarboxylation at 120 C. in a vacuum, dissolution in heptane, purification in CPC.

[0078] 1. CPC

[0079] 1st run: Quantitative separation of CBN, proportional separation of CBC:

[0080] Mobile phase: Acetonitrile TBME approx. 12%

[0081] Stationary phase: heptane TBME approx. 10%

[0082] From dronabinol 84.1% with approx. 15.9% impurities, wherein 5.4% is CBN and 2.2% is CBC.

[0083] Color: Dark brown to black.

[0084] FIG. 1

[0085] Result:

[0086] Dronabinol 97.7% with approx. 2.3% impurities, wherein 0.4% is CBM and 0,9% is CBC.

[0087] Color: Yellow

[0088] FIG. 2

[0089] Optional 2.sup.nd run: Quantitative purification of CBC

[0090] Mobile phase: acetonitrile TBME approx. 12%

[0091] Stationary phase: heptane TEME approx. 10%

[0092] From dronabinol 97.7% with approx. 2.3% impurities, wherein 0.8% is CEN and. 0,9% is CBC.

[0093] Color: Yellow

[0094] FIG. 3

[0095] Result:

[0096] Dronabinol 99.6% with approx. 0.4% impurities, wherein 0.04% is CBN and 0.05% is CBC.

[0097] Color: Yellowish (additional brightening)

[0098] FIG. 4

Example 2

CPC with Subsequent Run through Silica Gel Comma

[0099] Run: Quantitative separation of CBN

[0100] No separation of CBC.

[0101] Mobile phase: acetonitrile, purum

[0102] Stationary phase: heptane, purum

[0103] From dronabinol 81% with approx. 19% impurities, wherein 4.2% is CBN and 1.6% is CBC.

[0104] Color blackish to dark brown

[0105] FIG. 5

[0106] Result:

[0107] Dronabinol 94.5% with approx. 5.5% impurities, wherein 0.16% is CEN and 1.4% is CBC.

[0108] Color: Yellow

[0109] FIG. 6

[0110] Then preparative chromatography using silica gel for quantitative separation of CEO:

[0111] Mobile phase heptane 3% TBME

[0112] From dronabinol 96.4% with approx. 3.6% impurities, wherein 0.36% is CBN and 1.8% is CBC.

[0113] Color: Yellow

[0114] FIG. 7

[0115] Result:

[0116] Dronabinol 98.6% with approx. 1.4% impurities, wherein 0.4% is CBN and 0.0% is CBC.

[0117] Color: Colorless

[0118] FIG. 8:

[0119] Result:

[0120] Cannabidiol 99.3% with approx. 0.7% impurities, wherein 0.3% is CBN.

[0121] Color: Colorless, crystallizable

[0122] FIG. 9

[0123] Result:

[0124] Cannabichromene 94.1% with approx. 5.9% impurities, wherein drohabinol is 3.39% and 8-THC is 0.19%.