IP Library › Granted Patent US 8,829,215
Granted Patent B2
US 8,829,215 · App. 12/992,365 · Granted Sep 9, 2014

Krill oil process

Inventors: Harald Breivik (Porsgrunn, NO); Olav Thorstad (Porsgrunn, NO)
Assignee: Pronova Biopharma Norge AS
C11B1/104A23L1/3008A23D9/02C11B1/10A61K35/612C11B3/12C11B7/0083C11B1/02A23D9/013
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Quick Facts
Patent No.
US 8,829,215
App. No.
12/992,365
Granted
Sep 9, 2014
Kind
B2
Abstract

The present invention relates to a process for preparing compositions of high concentrations of omega-3 fatty acids from krill. Furthermore, the invention relates to a composition comprising high concentrations of omega-3 fatty acids, and a lipid fraction from krill comprising high amounts of fatty acids with chain length C14 and C16.

Claims (42)

1. A process for preparing a composition comprising a high concentration of omega-3 fatty acids, the process comprising:

a) reducing the water content of a krill raw material;

b) isolating the lipid fraction from the krill raw material to obtain a substantially total lipid fraction

c) subjecting the lipid fraction to an ethylation step to form ethyl esters; and

d) subjecting the lipid fraction to short path distillation or to one or more steps of supercritical fluid extraction, chromatography, or a combination thereof.

2. The process of claim 1 , wherein step a) comprises washing the krill raw material with at least one alcohol chosen from ethanol, methanol, propanol, iso-propanol, and any combination thereof in a weight ratio of krill material:alcohol ranging from 1:0.5 to 1:5; and step b) comprises isolating the lipid fraction from the at least one alcohol.

3. The process of claim 2 , wherein step a) comprises washing the krill raw material with ethanol; and step b) comprises isolating the lipid fraction from the ethanol.

4. The process of claim 1 , further comprising the step:

a-1) extracting the water reduced krill raw material from step a) with CO 2 at supercritical pressure containing at least one alcohol chosen from ethanol, methanol, propanol, iso-propanol, and a combination thereof;

wherein step a-1) is performed after step a) and before step b).

5. The process of claim 2 , wherein the krill raw material is heated to a temperature ranging from 60° C. to 100° C. before washing with the at least one alcohol.

6. The process of claim 5 , wherein the krill raw material is heated to a temperature ranging from 70° C. to 100° C. before washing with the at least one alcohol.

7. The process of claim 6 , wherein the krill raw material is heated to a temperature ranging from 80° C. to 95° C. before washing with the at least one alcohol.

8. The process of claim 1 , wherein the krill raw material is pre-treated by use of microwaves before washing.

9. The process of claim 2 , wherein washing the krill raw material with the at least one alcohol in step a) produces an extract rich in omega-3 fatty acids, and

removing residual alcohol from the krill material in step b) produces an extract low in omega-3 fatty acids.

10. The process of claim 9 , wherein the removal of residual alcohol from the krill material in step b) is carried out by pressing, centrifugation, or a combination thereof.

11. The process of claim 1 , wherein the short path distillation is a one-step or two-step short path distillation.

12. The process of claim 1 , further comprising the step:

e) subjecting the lipid fraction of step d) to mild urea fractionation.

13. The process of claim 12 , wherein the urea to ethyl ester ratio ranges from 0.1 to 1.5.

14. The process of claim 13 , wherein the urea to ethyl ester ratio ranges from 0.5 to 1.0.

15. The process of claim 12 , further comprising the step:

f) subjecting the lipid fraction of step e) to short path distillation.

16. A composition derived from krill comprising at least 75% by weight of at least one of eicopentaenoic acid (EPA) and docosahexaenoic acid (DHA), wherein the omega-3/omega-6 fatty acid ratio is greater than 30.

17. The composition of claim 16 , wherein the composition comprises at least 80% by weight of at least one of EPA and DHA.

18. The composition of claim 16 , wherein the composition comprises at least 90% by weight of omega-3 fatty acids.

19. The composition of claim 17 , wherein the weight ratio of EPA to DHA ranges from 1:2 to 2:1.

20. The composition of claim 16 , wherein the composition comprises a combination of EPA and DHA.

21. The composition of claim 16 , wherein at least one of the EPA and DHA is present in acid or ethyl ester form.

22. The composition of claim 16 , wherein the omega-3/omega-6 fatty acid ratio is greater than 40.

23. The composition of claim 22 , wherein the omega-3/omega-6 fatty acid ratio is greater than 50.

24. The composition of claim 16 , wherein the concentration of the fatty acid C22:5 n-6 is below 0.8% by weight with respect to the total composition weight.

25. A lipid fraction from krill comprising:

greater than 25% by weight of at least one fatty acid with a chain length chosen from C14 and C16, with respect to the total lipid fraction weight; and

greater than 30% by weight of at least one of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) with respect to the total lipid fraction weight.

26. The lipid fraction of claim 25 , comprising greater than 35% by weight of at least one of EPA and DHA with respect to the total lipid fraction weight.

27. The lipid fraction of claim 25 , comprising greater than 40% by weight of at least one of EPA and DHA with respect to the total lipid fraction weight.

28. The lipid fraction of claim 25 , wherein the lipid fraction is substantially free from the fatty acid C22:5 n-6.

29. A krill oil supplement product comprising the lipid fraction of claim 25 .

30. The process of claim 1 , wherein the lipid fraction is used as a start material in further process steps in order to achieve a high concentrate omega-3 acid or ester product.

31. The process of claim 30 , wherein the high concentrate omega-3 acid or ester product is an omega-3 supplement product or a pharmaceutical composition.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2011
From: BREIVIK, HARALD; THORSTAD, OLAV
To: PRONOVA BIOPHARMA NORGE AS
Reel/Frame 025796/0502 →
Continuity (2)
Provisional Application 61053455 · May 15, 2008
Related Publication 20110130458A1 · Jun 2, 2011