IP Library Granted Patent US 12660835
Granted Patent B2
US 12660835 · App. 18/150,443 · Granted Jun 23, 2026

Stabilized oil and methods of making the same

Inventors: Steven Lee Hansen (Chanhassen, MN); Diliara Iassonova (Maple Grove, MN); Gregg Perri (Plymouth, MN); Ying Joy Zhong (Olathe, KS)
Assignee: Cargill, Incorporated
A23D7/0053A23D7/04C11B5/00C11B5/0007C11B5/0028C11B5/0035C11B5/0071C11B5/0085
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Quick Facts
Patent No.
US 12660835
App. No.
18/150,443
Filed
Jan 5, 2023
Granted
Jun 23, 2026
Kind
B2
Art Unit
1792
USPC
426/601
Abstract

Stabilized oils including an edible oil and an antioxidant composition comprising α-lipoic acid and least one of ascorbic acid, ascorbyl palmitate, green tea extract, lecithin, and rosemary extract or at least one of 1,2,4-benzenetriol, carnosic acid, dihydromyricetin, dihydrorobinetin, epigallocatechin, gallic acid, 3-hydroxytyrosol, myricetin, and nepodin, and methods of preparing such stabilized edible oils. The stabilized oils may have an Oxidative Stability Index (“OSI”) at 110° C. of at least 30 hours.

Claims (47)

1 . A stabilized oil comprising:

an edible oil; and

an antioxidant composition,

wherein the antioxidant composition comprises:

α-lipoic acid;

at least one of 1,2,4-benzenetriol, carnosic acid, dihydromyricetin, dihydrorobinetin, epigallocatechin, gallic acid, myricetin, and nepodin; and

no more than 1600 ppm of phospholipid based on a total amount of the stabilized oil, wherein the stabilized oil has an α-lipoic acid concentration of from about 100 ppm to about 2,000 ppm.

2 . The stabilized oil of claim 1 , wherein the edible oil comprises a soybean oil, a palm oil, a canola oil, a corn oil, an olive oil, a peanut oil, a sunflower oil, a sesame oil, a safflower oil, a marine oil, or mixtures thereof.

3 . The stabilized oil of claim 2 , wherein the edible oil comprises a polyunsaturated fat selected from the group consisting of ALA, EPA, and DHA.

4 . The stabilized oil of claim 1 , wherein the stabilized oil has an α-lipoic acid concentration of from about 200 ppm to about 1,000 ppm.

5 . The stabilized oil of claim 1 , comprising from about 200 ppm to about 1,000 ppm 1,2,4-benzentriol.

6 . The stabilized oil of claim 1 , comprising about 1,000 ppm α-lipoic acid and about 1,000 ppm carnosic acid.

7 . The stabilized oil of claim 1 , comprising from about 200 ppm to about 500 ppm dihydromyricetin.

8 . The stabilized oil of claim 1 , comprising from about 200 ppm to about 1,000 ppm dihydrorobinetin.

9 . The stabilized oil of claim 1 , comprising from about 200 ppm to about 500 ppm epigallocatechin.

10 . The stabilized oil of claim 1 , comprising from about 200 ppm to about 1,000 ppm gallic acid.

11 . The stabilized oil of claim 1 , comprising from about 200 ppm to about 500 ppm myricetin.

12 . The stabilized oil of claim 1 , comprising from about 200 ppm to about 500 ppm nepodin.

13 . A method for preparing a stabilized oil, the method comprising:

providing an edible oil; and

adding an antioxidant composition to the edible oil to provide a stabilized oil, the antioxidant composition comprising:

α-lipoic acid;

at least one of 1,2,4-benzenetriol, carnosic acid, dihydromyricetin, dihydrorobinetin, epigallocatechin, gallic acid, myricetin, and nepodin; and

no more than 1600 ppm of phospholipid based on a total amount of the stabilized oil, wherein the stabilized oil has an α-lipoic acid concentration of from about 100 ppm to about 2,000 ppm.

14 . The method of claim 13 , wherein the edible oil comprises a soybean oil, a palm oil, a canola oil, a corn oil, an olive oil, a peanut oil, a sunflower oil, a sesame oil, a safflower oil, a marine oil, or mixtures thereof.

15 . The method of claim 13 , wherein the edible oil comprises a polyunsaturated fat selected from the group consisting of ALA, EPA, and DHA.

16 . The method of claim 13 , wherein the stabilized oil has an α-lipoic acid concentration from about 200 ppm to about 1,000 ppm.

17 . The method of claim 13 , wherein the stabilized oil has a 1,2,4-benzenetriol concentration of from about 200 ppm to about 1,000 ppm.

18 . The method of claim 13 , wherein the stabilized oil has an α-lipoic acid concentration of about 1,000 ppm and a carnosic acid concentration of about 1,000 ppm.

19 . The method of claim 13 , comprising from about 200 ppm to about 500 ppm dihydromyricetin.

20 . The method of claim 13 , comprising from about 200 ppm to about 1,000 ppm dihydrorobinetin.

21 . The method of claim 13 , wherein the stabilized oil has an epigallocatechin concentration of from about 200 ppm to about 500 ppm.

22 . The method of claim 13 , wherein the stabilized oil has a gallic acid concentration of from about 200 ppm to about 1,000 ppm.

23 . The method of claim 13 , wherein the stabilized oil has a myricetin concentration of from about 200 ppm to about 500 ppm.

24 . The method of claim 13 , wherein the stabilized oil has from about 200 ppm to about 500 ppm nepodin.

25 . The method of claim 13 , wherein the stabilized oil has an Oxidative Stability Index at 110° C. of at least 30 hours.

26 . A stabilized oil comprising:

an edible oil; and

an antioxidant composition,

wherein the antioxidant composition comprises:

α-lipoic acid;

at least one of 1,2,4-benzenetriol, carnosic acid, dihydromyricetin, dihydrorobinetin, epigallocatechin, gallic acid, myricetin, and nepodin; and

no more than 1600 ppm of phospholipid based on a total amount of the stabilized oil, wherein the stabilized oil has an α-lipoic acid concentration of from about 100 ppm to about 2,000 ppm, and

wherein the stabilized oil has at least a synergistic amount of the at least one of 1,2,4-benzenetriol, carnosic acid, dihydromyricetin, dihydrorobinetin, epigallocatechin, gallic acid, myricetin, and nepodin.

27 . The stabilized oil of claim 1 , wherein the phospholipid comprises one or more of phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol, and wherein the phospholipid is included in the stabilized oil at a concentration of 400 ppm to 1500 ppm.

28 . The method of claim 13 , wherein the phospholipid comprises one or more of phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol, and wherein the phospholipid is included in the stabilized oil at a concentration of 400 ppm to 1500 ppm.

29 . The stabilized oil of claim 26 , wherein the phospholipid comprises one or more of phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol, and wherein the phospholipid is included in the stabilized oil at a concentration of 400 ppm to 1500 ppm.