IP Library › Granted Patent US 11,649,221
Granted Patent B2
US 11,649,221 · App. 16/916,920 · Granted May 16, 2023

Method of isolating tetrahydrocannabinol from

Inventors: Jungyeob Ham (Gangneung-si, KR); Taejung Kim (Gangneung-si, KR); Bong Chul Chung (Seoul, KR); Sungdo Ha (Gangneung-si, KR); Seok Lee (Seoul, KR); Deok Ha Woo (Seoul, KR); Pilju Choi (Gangneung-si, KR); Bong Geun Song (Gangneung-si, KR)
Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY
C07D311/80A23L33/105A61K8/498A61Q19/00B01D11/0211B01D11/0288A23V2002/00A61K2800/10
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Quick Facts
Patent No.
US 11,649,221
App. No.
16/916,920
Granted
May 16, 2023
Kind
B2
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.

Claims (15)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 30, 2020
From: HAM, JUNGYEOB; KIM, TAEJUNG; CHUNG, BONG CHUL; HA, SUNGDO; LEE, SEOK; WOO, DEOK HA; CHOI, PILJU; SONG, BONG GEUN
To: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY
Reel/Frame 053092/0870 →
Priority Claims (1)
KR 10-2019-0078957 · Jul 1, 2019 · national
Continuity (1)
Related Publication 20210002247A1 · Jan 7, 2021