IP Library › Granted Patent US 11,582,982
Granted Patent B2
US 11,582,982 · App. 16/746,700 · Granted Feb 21, 2023

Method of making monoacylglyceride oils and food products containing monoacylglyceride oils

Inventors: Daniel J. Monticello (The Woodlands, TX); Werner J. Bussman (Houston, TX)
Assignee: GLYCOSBIO INC.
A23D7/011A23D7/015A23L29/06A23L33/15
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Quick Facts
Patent No.
US 11,582,982
App. No.
16/746,700
Granted
Feb 21, 2023
Kind
B2
Abstract

Compositions and methods are provided for incorporating processed oils with high monoacylglyceride (MAG) content into products and food products. Methods are specifically provided for generating high MAG content processed oils.

Claims (23)

1. A method for making a monoacylglycerol-enriched oil, comprising:

mixing a starting oil comprising triacylglycerols (TAGs), wherein the TAGs are in an amount greater than 50% by weight based on total weight of the starting oil, and wherein the starting oil is either free of monoacylglycerols (MAGs) or are present in an amount less than 5% by weight based on the total weight of the starting oil, a buffer solution and a first enzyme capable of hydrolyzing said TAGs to free fatty acids (FFAs) to yield a first reaction mixture;

allowing said first reaction mixture to react under conditions sufficient for said first enzyme to hydrolyze said TAGs for a first period of time to yield an aqueous phase and a first lipid reaction product comprising FFAs;

inactivating said first enzyme in said first lipid reaction product;

collecting said first lipid reaction product by removing said first lipid reaction product from the aqueous phase;

mixing said first lipid reaction product with a food-grade glycerol and a second enzyme capable of esterifying the FFAs to form a second reaction mixture;

allowing said second reaction mixture to react for a second period of time to yield a second lipid reaction product comprising a lipid oil phase and a glycerol phase, wherein water is removed from the second reaction mixture during the second period of time;

inactivating said second enzyme in said second lipid reaction product;

adding salt to the second lipid reaction product and separating the lipid oil phase from said glycerol phase; and

collecting said lipid oil phase, wherein the lipid oil phase comprises MAGs, diacylglycerols (DAGs), and free fatty acids (FFAs), wherein the MAGs are in an amount from about 30% to about 90% by weight based on total weight of the lipid oil phase, wherein the DAGs constitute from about 10% to about 30% by weight of the total weight of the lipid oil phase, wherein the FFAs constitutes from about 5% to about 60% by weight of the total weight of the lipid oil phase, and wherein the lipid oil phase either is free of TAGs or comprises TAGs in an about from about 0.1% to about 5% by weight based on the total weight of the lipid oil phase.

2. The method of claim 1 , wherein the starting oil is from about 1.00 mg/kg to about 12.00 mg/kg of monochloropropandiol (MCPD), wherein the lipid oil phase is substantially free of MCPD.

3. The method of claim 1 , wherein said starting oil is an oil derived from plant, animal or fish origin.

4. The method of claim 1 , wherein said starting oil is a plant oil selected from the group consisting of olive oil, sunflower oil, corn oil, almond oil, rapeseed oil, palm oil, soybean oil, flaxseed oil, and mixtures thereof.

5. The method of claim 1 , wherein said first enzyme is a lipase.

6. The method of claim 1 , wherein said buffer solution is a sodium citrate solution.

7. The method of claim 1 , wherein said first period of time is between about 14 and about 24 hours.

8. The method of claim 1 , wherein allowing said first reaction mixture to react under conditions sufficient for said first enzyme to hydrolyze said TAGs is performed at a temperature between about 30° C. and about 35° C.

9. The method of claim 1 , wherein said second enzyme is a lipase.

10. The method of claim 1 , wherein the first and second enzymes are each lipases, but different lipases.

11. The method of claim 1 , wherein said second period of time is between about 24 hours and about 72 hours.

12. The method of claim 1 , wherein allowing said second reaction mixture to react for the second period of time to yield the lipid oil phase and the glycerol phase is performed at a temperature between about 17° C. and 23° C.

13. The method of claim 1 , wherein the inactivating of said second enzyme is performed by heating said second lipid reaction product.

14. The method of claim 13 , wherein said heating is performed at a temperature of at least 70° C. for at least 1 hour.

Assignments (3)
CHANGE OF NAME Recorded Jun 24, 2021
From: GLYCOSBIO FOOD SCIENCES, INC.
To: GLYCOSBIO INC.
Reel/Frame 056666/0049 →
SECURITY INTEREST Recorded May 28, 2021
From: GLYCOSBIO INC.
To: WOODFOREST NATIONAL BANK
Reel/Frame 056385/0541 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2020
From: BUSSMANN, WERNER J.; MONTICELLO, DANIEL J.
To: GLYCOSBIO FOOD SCIENCES, INC.
Reel/Frame 053110/0973 →
Continuity (5)
Continuation In Part PCTUS2018055583 · Oct 12, 2018
Provisional Application 62833558 · Apr 12, 2019
Provisional Application 62794412 · Jan 18, 2019
Provisional Application 62571910 · Oct 13, 2017
Related Publication 20200146307A1 · May 14, 2020