Method of isolating tetrahydrocannabinol from Cannabis plant and use thereof

Patent metadata

Field	Value
Publication number	US-11649221-B2
Application number	US-202016916920-A
Country	US
Kind code	B2
Filing date	Jun 30, 2020
Priority date	Jul 1, 2019
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

Provided are a method of preparing a cannabis processed product having an increased Δ9-THC content in an efficient and economic manner, through a cyclization reaction by microwave irradiation of cannabis using various extraction solvents, and use of the processed product having an increased Δ9-THC content prepared by the method, a fraction thereof, and a single ingredient of THC, in foods, drugs, and cosmetics.

First claim

What is claimed is:

1. A method of isolating Δ9-tetrahydrocannabinol (THC) from a cannabis plant, the method comprising:
irradiating microwaves to a reaction mixture comprising a cannabidiol (CBD)-comprising sample, a Lewis acid, and a solvent in an airtight container;
wherein the microwave irradiation is carried out at 50° C. to 100° C., 1 atm to 15 atm, and for 10 min to 90 min;
wherein the solvent is ethyl acetate or a mixture of ethyl acetate and water; and
wherein the Lewis acid is para-toluenesulfonic acid, methanesulfonic acid, or camphor-10-sulfonic acid.

2. The method of claim 1 , wherein a concentration of the Lewis acid is 0.004 M to 0.12 M.

3. The method of claim 1 , wherein the CBD-comprising sample is obtained by a method including irradiating microwaves to a mixture comprising cannabis leaves or a solvent extract thereof and a solvent in an airtight container, or the solvent extract is obtained by a method including incubating a reaction mixture comprising cannabis leaves and a solvent.

4. The method of claim 1 , wherein a product obtained by the microwave irradiation has higher selectivity for Δ9-THC than Δ8-THC or iso-THC.

5. The method of claim 1 , further comprising isolating Δ9-THC from the reaction product obtained by the microwave irradiation.

6. The method of claim 3 , wherein the solvent for obtaining the CBD-comprising sample is C1-C6 alcohol, C3-C10 ester, C3-C10 ketone, C1-C6 unsubstituted or halogenated hydrocarbon, C2-C10 cyclic ether, a mixture thereof, or a mixture of one or more of the solvents and water.

7. The method of claim 3 , wherein the microwave irradiation for obtaining the CBD-comprising sample is carried out at 80° C. to 150° C.

8. The method of claim 3 , wherein the microwave irradiation for obtaining the CBD-comprising sample is carried out at 1 atm to 100 atm.

9. The method of claim 3 , wherein the microwave irradiation for obtaining the CBD-comprising sample is carried out for 5 min to 180 min.

10. The method of claim 3 , wherein the solvent for obtaining the CBD-comprising sample is ethyl acetate.

11. The method of claim 3 , wherein, in the product obtained by the microwave irradiation, a ratio of Δ8-THC:Δ9-THC is 1.0:1.6 to 3.5, based on the weight.

Assignees

• Korea Inst Sci & Tech

Inventors

• Ham Jungyeob
• Kim Taejung
• Chung Bong Chul
• Ha Sungdo
• Lee Seok
• Woo Deok Ha
• Choi Pilju
• Song Bong Geun

Classifications

• A61K8/498

  having 6-membered rings or their condensed derivatives, e.g. coumarin · CPC title

• A61K2800/10

  General cosmetic use · CPC title

• B01D11/0211

  in combination with an electric or magnetic field · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title