IP Library › Granted Patent US 12,458,036
Granted Patent B2
US 12,458,036 · App. 14/446,218 · Granted Nov 4, 2025

Oxidatively stable polyunsaturated fatty acid containing oil

Inventors: Michael Lenn Stefanski (Winchester, KY); Xuejun Tang (Ellicott City, MD); Kristine Sheila Crawford (Ellicott City, MD)
Assignee: DSM IP Assets B.V.
A23B2/733A23B2/771A23B20/30A23D9/007A23L27/82A23L33/115C11B5/0007C11B5/0085C11B5/0092A23V2002/00
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Quick Facts
Patent No.
US 12,458,036
App. No.
14/446,218
Granted
Nov 4, 2025
Kind
B2
Abstract

An oil comprising (i) at least 30 wt. % of one or more polyunsaturated fatty acids having at least 4 double bonds; (ii) at least one first antioxidant; and (iii) less than about 1000 ppm lecithin. The oil may comprise less than about 750 ppm of a second antioxidant chosen from an ascorbic acid derivative.

Claims (46)

1 . An oil comprising

(a) at least 30 wt. % of polyunsaturated fatty acids having at least 4 double bonds,

wherein the polyunsaturated fatty acids having at least 4 double bonds comprise a mixture of docosahexaenoic acid (DHA), omega-6 docosapentaenoic acid (DPA n-6), and eicosapentaenoic acid (EPA);

(b) at least one first antioxidant,

wherein the at least one first antioxidant comprises a tocopherol in an amount ranging from about 900 ppm to about 3400 ppm;

(c) less than 10 ppm lecithin; and

(d) less than 1 ppm of an ascorbic acid derivative,

wherein the oil has a peroxide value (POV) of from 0.4 to 5, an anisidine value (AnV) less than 20, and a Rancimat value of from 4.1 to 19.

2 . The oil of claim 1 , wherein said oil comprises less than 30 ppb iron.

3 . The oil of claim 1 , wherein said oil further comprises a flavoring reagent.

4 . The oil of claim 3 , wherein said flavoring reagent is rosemary extract.

5 . The oil of claim 1 , wherein said oil has a fishy aromatics sensory value of less than 1.5.

6 . The oil of claim 1 , wherein said oil has a fishy aromatics sensory value of less than 2.5.

7 . The oil of claim 1 , wherein said at least one first antioxidant comprises an additional tocopherol.

8 . The oil of claim 1 , wherein said at least one first antioxidant comprises a mixed tocopherol.

9 . The oil of claim 1 , wherein said oil is obtained from at least one microalgae, fish, plant, seed, or combinations thereof.

10 . The oil of claim 9 , wherein said oil is obtained from the at least one microalgae and the at least one microalgae comprises microalgae from the order Thraustochytriales.

11 . The oil of claim 10 , wherein said microalgae is a Thraustochytrium sp., Schizochytrium sp., or combinations thereof.

12 . The oil of claim 1 , wherein said oil is obtained from a plant.

13 . The oil of claim 1 , wherein said oil is obtained from fish.

14 . A final oil comprising the oil of claim 1 and at least one further oil.

15 . The final oil of claim 14 , wherein said further oil is a vegetable oil.

16 . The final oil of claim 1 , wherein said oil is an edible oil.

17 . A food product comprising the oil of claim 1 .

18 . The oil of claim 1 , wherein said oil comprises at least 35 wt. % of DHA.

19 . The oil of claim 1 , wherein said oil has a fishy aromatics value of less than 1.5 at a time period between 0-9 months.

20 . The oil of claim 1 , wherein said oil has a fishy aromatics value of less than 2.5 at a time period between 0-9 months.

21 . The oil of claim 1 , wherein said oil comprises tocopherol in an amount ranging from about 1000 ppm to 3000 ppm.

22 . The oil of claim 1 , wherein said oil comprises an additional tocopherol ranging from about 300 ppm to about 1000 ppm.

23 . The oil of claim 1 , wherein said oil further comprises rosemary extract in an amount ranging from 1500 ppm to 5000 ppm.

24 . The oil of claim 1 , wherein said oil has an anisidine value (AnV) less than 10.

25 . The oil of claim 1 , wherein said oil comprises at least 40 wt. % of DHA.

26 . The oil of claim 1 , wherein said oil comprises at least 45 wt. % of DHA.

27 . The oil of claim 1 , wherein said oil comprises at least 50 wt. % of DHA.

28 . The oil of claim 1 , wherein said oil comprises less than 80 wt. % of DHA.

29 . The oil of claim 1 , wherein said oil comprises less than 70 wt. % of DHA.

30 . The oil of claim 1 , wherein said oil comprises less than 60 wt. % of DHA.

31 . The oil of claim 1 , wherein said oil further comprises arachidonic acid (ARA).

32 . An oil from at least one microalgae from the order Thraustochytriales, comprising

(a) at least 30 wt. % of polyunsaturated fatty acids having at least 4 double bonds,

wherein the polyunsaturated fatty acids having at least 4 double bonds comprise a mixture of docosahexaenoic acid (DHA), omega-6 docosapentaenoic acid (DPA n-6), and eicosapentaenoic acid (EPA);

(b) at least one first antioxidant,

wherein the at least one first antioxidant is a tocopherol and the oil comprises tocopherol in an amount ranging from about 900 ppm to about 3400 ppm; and

(c) less than 10 ppm lecithin, and

(d) less than 1 ppm of an ascorbic acid derivative,

wherein the oil has a peroxide value (POV) of from 0.4 to 5, an anisidine value (AnV) less than 20, and a Rancimat value of from 4.1 to 19.

Assignments (2)
CHANGE OF ASSIGNEE ADDRESS. Recorded Sep 12, 2025
From: DSM IP ASSETS B.V.
To: DSM IP ASSETS B.V.
Reel/Frame 072885/0943 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2014
From: STEFANSKI, MICHAEL LENN; CRAWFORD, KRISTINE SHEILA; TANG, XUEJUN
To: DSM IP ASSETS B.V.
Reel/Frame 033902/0941 →
Continuity (3)
Continuation 13694134 · Nov 1, 2012
Provisional Application 61554291 · Nov 1, 2011
Related Publication 20150017304A1 · Jan 15, 2015
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