IP Library Granted Patent US 11,807,890
Granted Patent B2
US 11,807,890 · App. 17/456,126 · Granted Nov 7, 2023

Methods for production of oxygenated terpenes

Inventors: Ajikumar Parayil Kumaran (Cambridge, SC); Chin Giaw Lim (Allston, MA); Liwei Li (Arlington, MA); Souvik Ghosh (Cambridge, MA); Christopher Pirie (Cambridge, MA); Anthony Qualley (Beavercreek, OH); Geoff Marshall-Hill (Buckinghamshire, GB); Martin Preininger (Neuss, DE)
Assignees: GIVAUDAN SA; MANUS BIO INC.
C12P7/26A01N27/00A23L27/13C12N9/0073C12P5/002C12Y114/13078A23V2002/00C07K2319/03
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Quick Facts
Patent No.
US 11,807,890
App. No.
17/456,126
Granted
Nov 7, 2023
Kind
B2
Abstract

The present disclosure relates to methods for producing oxygenated terpenoids, and preparation of compositions and formulations thereof. Polynucleotides, derivative enzymes, and host cells for use in such methods are also provided.

Claims (26)

1. A product comprising:

an oxygenated terpene formulation comprising:

nootkatone in an amount ranging from about 55% to about 60% (w/w);

α-nootkatol in an amount ranging from about 20% to about 25% (w/w); and

β-nootkatol in an amount ranging from about 5% to about 10% (w/w),

wherein the product is a flavor product, a natural flavor product, a fragrance product, a cosmetic product, a cleaning product, a detergent product, a soap product, or a pest control product.

2. The product of claim 1 , wherein the flavor product is a natural flavor, beverage, a chewing gum, a candy, an artificial flavor, or a flavor additive.

3. The product of claim 1 , wherein the formulation further comprises valencene.

4. The product of claim 3 , wherein the valencene is present in the oxygenated terpene formulation in an amount ranging from about 5% to about 10% (w/w).

5. The product of claim 1 , wherein at least one of the nootkatone, the α-nootkatol, and the β-nootkatol, is produced using a biosynthetic process.

6. The product of claim 1 , wherein the nootkatone, the α-nootkatol, and the β-nootkatol, are produced using at least one biosynthetic process.

7. A method of making a product for providing oxygenated terpenes, comprising:

obtaining a formulation, said formulation comprising:

nootkatone in an amount ranging from about 55% to about 60% (w/w);

α-nootkatol in an amount ranging from about 20% to about 25% (w/w); and

β-nootkatol in an amount ranging from about 5% to about 10% (w/w), and

incorporating the formulation into a consumer product, an industrial product, a flavor product, a fragrance product, a cosmetic product, a cleaning product, a detergent product, a soap product, or a pest control product.

8. The method of claim 7 , wherein the flavor product is a beverage, a chewing gum, a candy, a natural flavor, an artificial flavor, or a flavor additive.

9. The method of claim 7 , wherein obtaining the formulation comprises contacting valencene with Stevia rebaudiana Kaurene Oxidase (SrKO) or an SrKO derivative comprising a sequence having at least 70% sequence identity to SEQ ID NO: 37, SEQ ID NO: 38, or SEQ ID NO: 55, and having valencene oxidizing activity in an in vivo or in vitro system to yield an oxygenated product.

10. The method of claim 7 , further comprising processing the oxygenated product by fractional distillation to yield two or more fractions of the oxygenated product.

11. The method of claim 10 , further comprising blending the two or more fractions of the oxygenated product.

12. The method of claim 7 , further comprising adding an unoxygenated product to the oxygenated product, one or more fractions of the oxygenated product, or the formulation.

13. The method of claim 12 , wherein the unoxygenated product comprises valencene.

14. The method of claim 13 , wherein the valencene is present in the formulation in an amount ranging from about 5% to about 10% (w/w).

15. The method of claim 7 , wherein the formulation further comprises one or more non-sesquiterpene components or sesquiterpene components.

16. The method of claim 15 , wherein the one or more non-sesquiterpene components or sesquiterpene components is selected from Table 8A, Table 8B, and Table 9.

Assignments (6)
SECURITY INTEREST Recorded Sep 8, 2025
From: MANUS BIO INC.; STO.PERU I LLC; STO.PERU II LLC; MANUS INTERMEDIATE INC.; MANUS INSCRIPTA, INC.
To: SYMBIOTIC CAPITAL AGENCY LLC, AS ADMINISTRATIVE AND COLLATERAL AGENT
Reel/Frame 072836/0255 →
RELEASE OF SECURITY INTEREST Recorded May 9, 2025
From: EICF AGENT LLC
To: MANUS BIO INC.
Reel/Frame 071247/0658 →
CHANGE OF NAME Recorded May 18, 2022
From: MANUS BIOSYNTHESIS, INC.
To: MANUS BIO INC.
Reel/Frame 060108/0143 →
SECURITY AGREEMENT Recorded Apr 1, 2022
From: MANUS BIO INC.
To: EICF AGENT LLC
Reel/Frame 059568/0683 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2021
From: MARSHALL-HILL, GEOFF; PREININGER, MARTIN
To: GIVAUDAN SA
Reel/Frame 058204/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2021
From: KUMARAN, AJIKUMAR PARAYIL; LIM, CHIN GIAW; LI, LIWEI; GHOSH, SOUVIK; PIRIE, CHRISTOPHER; QUALLEY, ANTHONY
To: MANUS BIOSYNTHESIS, INC.
Reel/Frame 058204/0725 →
Continuity (4)
Continuation 16669051 · Oct 30, 2019
Division 15505022
Provisional Application 62040284 · Aug 21, 2014
Related Publication 20220073955A1 · Mar 10, 2022
Cited By (1)
US 12,545,934