Hydroxylated triacylglycerides

• US 9,109,239 B2
• Filed: 10/11/2012
• Issued: 08/18/2015
• Est. Priority Date: 05/28/2010
• Status: Active Grant

• Current Assignee: Corbion Biotech, Inc. (Corbion NV)
• Original Assignee: Solazyme Inc.
• Inventors: Franklin, Scott, Somanchi, Aravind, Wee, Janice, Rudenko, George, Moseley, Jeffrey L., Rakitsky, Walt
• Primary Examiner(s): Dye, Rena L
• Assistant Examiner(s): Zilbering, Assaf
• Application Number:
  US13/650,018
• Publication Number:
  US 20130096211A1
• Time in Patent Office: 1,041 Days
• Field of Search: 426/61, 521/921
• US Class Current: 1/1
• CPC Class Codes: A23D 7/00 Edible oil or fat compositions containing an aqueous phase, e.g. margarines
• CPC Class Codes: A23D 9/00 Other edible oils or fats, e.g. shortenings, cooking oils
• CPC Class Codes: A23K 20/158 Fatty acids; Fats; Products containing oils or fats
• CPC Class Codes: C11B 1/00 Production of fats or fatty oils from raw materials
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C12N 15/67 General methods for enhancing the expression
• CPC Class Codes: C12N 15/79 Vectors or expression systems specially adapted for eukaryotic hosts
• CPC Class Codes: C12N 15/8216 Methods for controlling, regulating or enhancing expression of transgenes in plant cells
• CPC Class Codes: C12N 9/0071 acting on paired donors with incorporation of molecular oxygen (1.14)
• CPC Class Codes: C12N 9/16 acting on ester bonds (3.1)
• CPC Class Codes: C12N 9/2431 Beta-fructofuranosidase (3.2.1.26), i.e. invertase
• CPC Class Codes: C12N 9/2465 acting on alpha-galactose-glycoside bonds, e.g. alpha-galactosidase (3.2.1.22)
• CPC Class Codes: C12P 7/64 Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
• CPC Class Codes: C12P 7/6445 Glycerides
• CPC Class Codes: C12P 7/6463 obtained from glyceride producing microorganisms, e.g. single cell oil
• CPC Class Codes: C12Y 114/19001 Stearoyl-CoA 9-desaturase (1.14.19.1), i.e. DELTA9-desaturase
• CPC Class Codes: C12Y 301/02 Thioester hydrolases (3.1.2)
• CPC Class Codes: C12Y 301/02014 Oleoyl-[acyl-carrier-protein] hydrolase (3.1.2.14), i.e. ACP-thioesterase
• CPC Class Codes: C12Y 302/01022 Alpha-galactosidase (3.2.1.22)
• CPC Class Codes: C12Y 302/01026 Beta-fructofuranosidase (3.2.1.26), i.e. invertase
• CPC Class Codes: Y02E 50/10 : Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02P 30/20 : using bio-feedstock
• CPC Class Codes: Y02T 50/678 : Aviation using fuels of non-fossil origin

Abstract

Methods and compositions for the production of food compositions, oils, fuels, oleochemicals, and other compounds in recombinant microorganisms are provided, including oil-bearing microorganisms and methods of low cost cultivation of such microorganisms. Microalgal cells containing exogenous genes encoding, for example, a lipase, a sucrose transporter, a sucrose invertase, a fructokinase, a polysaccharide-degrading enzyme, a keto acyl-ACP synthase enzyme, a fatty acyl-ACP thioesterase, a fatty acyl-CoA/aldehyde reductase, a fatty acyl-CoA reductase, a fatty aldehyde reductase, a fatty aldehyde decarbonylase, and/or an acyl carrier protein are useful in manufacturing food compositions, and transportation fuels such as renewable diesel, biodiesel, and renewable jet fuel, as well as oleochemicals such as functional fluids, surfactants, soaps and lubricants.

Claims

1. A composition produced by the process of hydroxylating a triacylglyceride oil obtained from a microalga, the microalga comprising an exogenous nucleic acid operable to reduce the activity of Δ

12 fatty acid desaturase in the microalga, the fatty acid profile of the triacylglyceride oil comprising less than 3% C18;

2 fatty acid and at least 60% C18;

1 fatty acid.

2. The composition of claim 1, wherein the hydroxylating is followed by a condensation reaction.

3. The composition of claim 1, wherein the triglyceride oil comprises less than 2% C18:

2 fatty acid.

4. The composition of claim 1, wherein the triglyceride oil comprises less than 1% C18:

2 fatty acid.

5. The composition of claim 1, wherein the composition is a polyurethane.

6. The composition of claim 2, wherein the composition is a polyurethane.

7. The composition of claim 3, wherein the composition is a polyurethane.

8. The composition of claim 4, wherein the composition is a polyurethane.

9. The composition of claim 1, wherein the composition is a coating.

10. The composition of claim 1, wherein the composition is an ink.

11. The composition of claim 1, wherein the composition is a lubricant.

12. The composition of claim 1, wherein the composition is a cosmetic.

13. The composition of claim 1, wherein the composition is an estolide.

14. The composition of claim 1, wherein the triglyceride oil comprises less than 2% C18:

2 fatty acid and at least 70% C18;

1.

15. The composition of claim 1, wherein the triglyceride oil comprises less than 2% C18:

2 fatty acid and at least 80% C18;

1.

16. The composition of claim 1, wherein the triglyceride oil comprises at least 5% C18:

0 fatty acid.

17. A composition produced by the process of hydroxylating a triacylglyceride oil obtained from a microalga and performing a condensation reaction on the hydroxylated triacylglyceride oil, the microalga comprising an exogenous nucleic acid operable to reduce the activity of Δ

12 fatty acid desaturase in the microalga, the fatty acid profile of the triacylglyceride oil obtained comprising less than 3% C18;

2 fatty acid and at least 60% C18;

1 fatty acid.

18. The composition of claim 17, wherein the composition is a polyurethane.

19. The composition of claim 17, wherein the composition is a coating.

20. The composition of claim 17, wherein the composition is an ink.

21. A composition produced by the process of hydroxylating a triacylglyceride oil obtained from a microalga and performing a condensation reaction on the hydroxylated triacylglyceride, the microalga comprising an exogenous nucleic acid operable to reduce the activity of Δ

12 fatty acid desaturase in the microalga, the fatty acid profile of the triacylglyceride oil obtained comprising less than 2% C18;

2 fatty acid, at least 70% C18;

1 fatty acid.