IP Library Granted Patent US 11,319,525
Granted Patent B2
US 11,319,525 · App. 16/453,578 · Granted May 3, 2022

Apparatus, methods and composition for synthesis of cannabinoid compounds

Inventors: Richard Peet (Washington, DC); Malcolm J. Kavarana (Fairfax, VA); Mingyang Sun (Dublin, IE); Peter C. Michels (Voorheesville, NY); John D. Rabenstein (Feura Bush, NY); C. Seth Pearson (Albany, NY); Geoffrey M. Fox (Voorheesville, NY)
Assignee: TEEWINOT LIFE SCIENCES CORPORATION
C12M41/30C12M1/34C12M1/36C12M1/40C12M21/18C12M23/58C12M41/12C12M41/26C12M41/40C12M41/48C12M47/10C12P7/42C12P17/06
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Quick Facts
Patent No.
US 11,319,525
App. No.
16/453,578
Granted
May 3, 2022
Kind
B2
Abstract

The disclosure provides systems and methods for producing a cannabinoid product, which comprises contacting a cannabinoid precursor in a first phase with a cannabinoid synthase in a second phase, wherein the first phase and the second phase are substantially immiscible or immiscible. The disclosure also provides a composition comprising the cannabinoid precursor in a first phase and a cannabinoid synthase in a second phase, wherein the first phase and the second phase are substantially immiscible or immiscible.

Claims (26)

1. A biphasic composition comprising:

(a) a cannabinoid precursor in a first phase, wherein the cannabinoid precursor is compound of Formula II:

wherein R 1 is H or COOH and R 2 is a linear or branched CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 5 H 10 , C 6 H 13 , C 7 H 15 or C 8 H 17 group; and

(b) a cannabinoid synthase in a second phase,

wherein the first phase comprises an organic solvent and the second phase comprises an aqueous solvent, and wherein the organic solvent comprises olive oil, sesame oil, castor oil, cotton-seed oil, soybean oil, pentane, heptane, octane, isooctane, nonane, decane, or terpene.

2. The biphasic composition of claim 1 , wherein the organic solvent comprises a terpene.

3. The biphasic composition of claim 1 , wherein the terpene comprises dipentene.

4. The biphasic composition of claim 1 , wherein the organic solvent comprises olive oil, sesame oil, castor oil, cotton-seed oil, or soybean oil.

5. The biphasic composition of claim 1 , wherein the aqueous solvent further comprises dimethyl sulfoxide (DMSO), dimethylformamide (DMF), dimethylacetamide (DMA), isopropyl alcohol, cyclodextrin, peroxide scavenger, or methanol (MeOH).

6. The biphasic composition of claim 1 , wherein the volume ratio of the first phase to the second phase is about 2:1.

7. The biphasic composition of claim 1 , wherein the aqueous solvent further comprises DMSO in a range between about 5% and about 10% of the aqueous solution, and wherein the pH value of the aqueous solution is between about 5.5 and about 7.5.

8. The biphasic composition of claim 1 , wherein the cannabinoid precursor is cannabigerolic acid (CBGA) or cannabigerovarinic acid (CBGVA).

9. The biphasic composition of claim 1 , wherein the cannabinoid synthase is CBDA synthase or THCA synthase.

10. A method for producing a cannabinoid product comprising:

contacting a cannabinoid precursor in a first phase with a cannabinoid synthase in a second phase, wherein the cannabinoid precursor is the compound of Formula II:

wherein R 1 is H or COOH and R 2 is a linear or branched CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 5 H 10 , C 6 H 13 , C 7 H 15 or C 8 H 17 group,

wherein the first phase comprises an organic solvent and the second phase comprises an aqueous solvent, and wherein the organic solvent comprises olive oil, sesame oil, castor oil, cotton-seed oil, soybean oil, pentane, heptane, octane, isooctane, nonane, decane, or terpene.

11. The method of claim 10 , wherein the organic solvent comprises a terpene.

12. The method of claim 11 , wherein the terpene comprises dipentene.

13. The method of claim 10 , wherein the organic solvent comprises olive oil, sesame oil, castor oil, cotton-seed oil, or soybean oil.

14. The method of claim 10 , wherein the aqueous solvent further comprises dimethyl sulfoxide (DMSO), dimethylformamide (DMF), dimethylacetamide (DMA), isopropyl alcohol, cyclodextrin, peroxide scavenger, or methanol (MeOH).

15. The method of claim 10 , wherein the volume ratio of the first phase to the second phase is about 2:1.

16. The method of claim 10 , wherein the aqueous solvent further comprises DMSO in a range between about 5% and about 10% of the aqueous solution, and wherein the pH value of the aqueous solution is between about 5.5 and about 7.5.

17. The method of claim 10 , wherein the cannabinoid precursor is cannabigerolic acid (CBGA) or cannabigerovarinic acid (CBGVA).

18. The method of claim 10 , wherein the cannabinoid synthase is CBDA synthase or THCA synthase.

19. The method of claim 10 further comprising agitating the first phase to form micro-droplets comprising the cannabinoid precursor.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2022
From: TEEWINOT TECHNOLOGIES LIMITED
To: TEEWINOT LIFE SCIENCES CORPORATION
Reel/Frame 059021/0539 →
SECURITY INTEREST Recorded Nov 23, 2021
From: TEEWINOT LIFE SCIENCES CORPORATION; TEEWINOT TECHNOLOGIES LIMITED
To: TUATARA CAPITAL FUND I, L.P.; TUATARA CAPITAL PARALLEL FUND I, L.P.
Reel/Frame 058194/0474 →
SECURITY INTEREST Recorded Nov 23, 2021
From: TEEWINOT TECHNOLOGIES LIMITED
To: TUATARA CAPITAL FUND I, L.P.; TUATARA CAPITAL PARALLEL FUND I, L.P.
Reel/Frame 058194/0448 →
SECURITY INTEREST Recorded Nov 22, 2021
From: TEEWINOT LIFE SCIENCES CORPORATION; TEEWINOT TECHNOLOGIES LIMITED
To: TUATARA CAPITAL FUND I, L.P.; TUATARA CAPITAL PARALLEL FUND I, L.P.
Reel/Frame 058182/0033 →
SECURITY INTEREST Recorded Nov 22, 2021
From: TEEWINOT TECHNOLOGIES LIMITED
To: TUATARA CAPITAL FUND I, L.P.; TUATARA CAPITAL PARALLEL FUND I, L.P.
Reel/Frame 058180/0377 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2021
From: PEET, RICHARD; KAVARANA, MALCOLM J.; MICHELS, PETER C.; RABENSTEIN, JOHN D.; PEARSON, C. SETH; FOX, GEOFFREY M.; SUN, MINGYANG
To: TEEWINOT TECHNOLOGIES LIMITED
Reel/Frame 056103/0021 →
SECURITY INTEREST Recorded Aug 24, 2020
From: TEEWINOT TECHNOLOGIES, LTD.
To: TUATARA CAPITAL FUND I, L.P.
Reel/Frame 053582/0897 →
Continuity (7)
Continuation 15976487 · May 10, 2018
Continuation PCTUS2018029638 · Apr 26, 2018
Provisional Application 62514626 · Jun 2, 2017
Provisional Application 62514617 · Jun 2, 2017
Provisional Application 62490577 · Apr 26, 2017
Provisional Application 62490579 · Apr 26, 2017
Related Publication 20190382708A1 · Dec 19, 2019