Process for producing ethyl esters of polyunsaturated fatty acids

Patent metadata

Field	Value
Publication number	US-9932541-B2
Application number	US-201715678009-A
Country	US
Kind code	B2
Filing date	Aug 15, 2017
Priority date	Jun 15, 2012
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

The present invention relates to a process for producing ethyl esters of polyunsaturated fatty acids, comprising transesterifying triacylglycerols in extracted plant lipid.

First claim

What is claimed is:

1. Oil extracted from seeds which are Brassica napus or Arabidopsis thaliana seeds, wherein the oil comprises a total fatty acid content which comprises
a) a total monounsaturated fatty acid content which comprises oleic acid,
b) a total saturated fatty acid content which comprises palmitic acid and, if present, myristic acid (C14:0),
c) a total ω6 fatty acid content which comprises linoleic acid (LA) and γ-linolenic acid (GLA), or palmitic acid and, arachidonic acid (ARA),
d) a total ω3 fatty acid content which comprises α-linolenic acid (ALA), docosahexaenoic acid (DHA), stearidonic acid (SDA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA) and eicosatetraenoic acid (ETA),
wherein
i) EPA, DPA and DHA, and optionally ARA, are each present at a level in the total fatty acid content, each level being expressed as a percentage of the total fatty acid content, whereby the sum total of the levels of ARA, EPA, DPA and DHA in the extracted oil is between 7% and 25% of the total fatty acid content,
ii) DHA is esterified in the form of triacylglycerols (TAG), wherein at least 70% of the DHA which is esterified in the form of TAG is esterified at the sn-1 or sn-3 position of the TAG,
iii) palmitic acid is present in the extracted oil at a level of between 2% and 16% of the total fatty acid content,
iv) oleic acid is present in the extracted oil at a level of between 1% and 30% of the total fatty acid content,
v) LA is present in the extracted oil at a level of between 4% and 35% of the total fatty acid content,
vi) GLA is present in the extracted oil at a level of less than 4% of the total fatty acid content,
vii) ALA is present in the extracted oil at a level of between 4% and 40% of the total fatty acid content,
viii) the total saturated fatty acid content of the extracted oil is between 4% and 25% of the total fatty acid content,
ix) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content of the extracted oil is between 0.1 and 3.0,
x) myristic acid, if present, is present at a level of less than 1% of the total fatty acid content, and
xi) eicosatrienoic acid (ETrA), if present, is present at a level of less than 4% of the total fatty acid content.

2. The oil of claim 1 , wherein γ-linolenic acid (GLA) is present in the extracted oil at a level of less than 2% of the total fatty acid content.

3. The oil of claim 1 , wherein oleic acid is present in the extracted oil at a level of between 3% and 30% of the total fatty acid content.

4. The oil of claim 1 , wherein the total saturated fatty acid content of the extracted oil is between 6% and 20% of the total fatty acid content.

5. The oil of claim 1 , comprising new ω3 fatty acids in the total ω3 fatty acid content and new ω6 fatty acids in the total ω6 fatty acid content, wherein the ratio of the new ω6 fatty acids to the new ω3 fatty acids in the extracted canola oil is between 0.1 and 1.

6. The oil of claim 1 , comprising tri-DHA TAG (TAG 66:18).

7. The oil of claim 1 , wherein at least 80% of the DHA esterified in the form of TAG is at the sn-1 or sn-3 position of the TAG.

8. The oil of claim 1 , wherein SDA, ETA, EPA, DPA and DHA are each present at a level in the total fatty acid content, each level being expressed as a percentage of the total fatty acid content, whereby the sum of the percentages for ETA, EPA, DPA and DHA divided by the sum of the percentages for SDA, ETA, EPA, DPA and DHA, expressed as a percentage, is at least 75%.

9. The oil of claim 1 , wherein ETA, EPA, DPA and DHA are each present at a level in the total fatty acid content, each level being expressed as a percentage of the total fatty acid content, whereby the sum of the percentages for EPA, DPA and DHA divided by the sum of the percentages for ETA, EPA, DPA and DHA, expressed as a percentage, is between 70% and 88%.

10. The oil of claim 1 , wherein DHA is present at a level of about 3% of the total fatty acid content.

11. The oil of claim 1 , wherein DHA is present at a level of about 4% of the total fatty acid content.

12. The oil of claim 1 , wherein DHA is present at a level of about 5% of the total fatty acid content.

13. The oil of claim 1 , wherein DHA is present at a level of about 6% of the total fatty acid content.

14. The oil of claim 1 , wherein DHA is present at a level of between 7% and 20% of the total fatty acid content.

15. Oil extracted from seeds which are Brassica napus or Arabidopsis thaliana seeds, wherein the oil comprises a total fatty acid content which comprises
a) a total monounsaturated fatty acid content which comprises oleic acid,
b) a total saturated fatty acid content which comprises palmitic acid and, if present, myristic acid (C14:0),
c) a total ω6 fatty acid content which comprises linoleic acid (LA) and γ-linolenic acid (GLA), and, or palmitic acid and, arachidonic acid (ARA),
d) a total ω3 fatty acid content which comprises α-linolenic acid (ALA), docosahexaenoic acid (DHA), stearidonic acid (SDA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA) and eicosatetraenoic acid (ETA),
wherein
i) EPA, DPA and DHA, and optionally ARA, are each present at a level in the total fatty acid content, each level being expressed as a percentage of the total fatty acid content, whereby the sum total of the levels of ARA, EPA, DPA and DHA in the extracted oil is between 7% and 25% of the total fatty acid content,
ii) DHA is esterified in the form of triacylglycerols (TAG), wherein at least 70% of the DHA which is esterified in the form of TAG is esterified at the sn-1 or sn-3 position of the TAG,
iii) palmitic acid is present in the extracted oil at a level of between 2% and 16% of the total fatty acid content,
iv) oleic acid is present in the extracted oil at a level of about 30% of the total fatty acid content,
v) LA is present in the extracted oil at a level of between 4% and 35% of the total fatty acid content,
vi) GLA is present in the extracted oil at a level of less than 4% of the total fatty acid content,
vii) ALA is present in the extracted oil at a level of between 4% and 40% of the total fatty acid content,
viii) the total saturated fatty acid content of the extracted oil is between 4% and 25% of the total fatty acid content,
ix) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content of the extracted oil is between 0.1 and 3.0,
x) myristic acid, if present, is present at a level of less than 1% of the total fatty acid content, and
xi) eicosatrienoic acid (ETrA), if present, is present at a level of less than 4% of the total fatty acid content.

16. The oil of claim 15 , wherein γ-linolenic acid (GLA) is present in the extracted oil at a level of less than 2% of the total fatty acid content.

17. The oil of claim 15 , wherein the total saturated fatty acid content of the extracted oil is between 6% and 20% of the total fatty acid content.

18. The oil of claim 15 , comprising new (03 fatty acids in the total ω3 fatty acid content and new ω6 fatty acids in the total ω6 fatty acid content, wherein the ratio of the new ω6 fatty acids to the new ω3 fatty acids in the extracted canola oil is between 0.1 and 1.

19. The oil of claim 15 , comprising tri-DHA TAG (TAG 66:18).

20. The oil of claim 15 , wherein at least 80% of the DHA esterified in the form of TAG is at the sn-1 or sn-3 position of the TAG.

21. The oil of claim 15 , wherein SDA, ETA, EPA, DPA and DHA are each present at a level in the total fatty acid content, ea

Assignees

• Commw Scient Ind Res Org
• Grains Res & Dev Corp
• Nuseed Pty Ltd
• Nuseed Pty Ltd

Inventors

• Petrie James Robertson
• Singh Surinder Pal
• De Feyter Robert Charles

Classifications

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P9/12

  Antihypertensives · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• A61P9/06

  Antiarrhythmics · CPC title