Process for producing ethyl esters of polyunsaturated fatty acids

Patent metadata

Field	Value
Publication number	US-9932290-B2
Application number	US-201715678005-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. A process for producing ethyl esters of polyunsaturated fatty acids, the process comprising transesterifying polyunsaturated fatty acids in triacylglycerols (TAG) in oil extracted from Brassica napus seeds 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, or palmitic acid and myristic acid (C14:0),
c) a total ω6 fatty acid content which comprises linoleic acid (LA) and γ-linolenic acid (GLA),
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) DHA is present in the extracted oil at a level of about 3% of the total fatty acid content, wherein at least 70% of the DHA which is esterified in the form of triacylglycerols (TAG) is esterified at the sn-1 or sn-3 position of the TAG,
ii) palmitic acid is present in the extracted oil at a level of between 2% and 15% of the total fatty acid content,
iii) oleic acid is present in the extracted oil at a level of between 1% and 30% of the total fatty acid content,
iv) LA is present in the extracted oil at a level of between 4% and 35% of the total fatty acid content,
v) GLA is present in the extracted oil at a level of less than 4% of the total fatty acid content,
vi) ALA is present in the extracted oil at a level of between 4% and 40% of the total fatty acid content,
vii) the total saturated fatty acid content of the extracted oil is between 4% and 25% of the total fatty acid content,
viii) 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,
ix) myristic acid, if present, is present at a level of less than 1% of the total fatty acid content, and
x) eicosatrienoic acid (ETrA), if present, is present at a level of less than 4% of the total fatty acid content,

thereby producing the ethyl esters.

2. The process of claim 1 , wherein γ-linolenic acid (GLA) is present in the extracted oil at a level of less than 3% of the total fatty acid content.

3. The process of claim 1 , wherein oleic acid is present in the extracted oil at a level of between 6% and 30% of the total fatty acid content.

4. The process 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 process of claim 1 , wherein the extracted oil comprises 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 process of claim 1 , wherein the extracted oil comprises tri-DHA TAG (TAG 66:18).

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

8. A process for producing ethyl esters of polyunsaturated fatty acids, the process comprising transesterifying polyunsaturated fatty acids in triacylglycerols (TAG) in oil extracted from Brassica napus seeds 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, or palmitic acid and myristic acid (C14:0),
c) a total ω6 fatty acid content which comprises linoleic acid (LA) and γ-linolenic acid (GLA),
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) DHA is present in the extracted oil at a level of about 4% of the total fatty acid content, wherein at least 70% of the DHA which is esterified in the form of triacylglycerols (TAG) is esterified at the sn-1 or sn-3 position of the TAG,
ii) palmitic acid is present in the extracted oil at a level of between 2% and 16% of the total fatty acid content,
iii) oleic acid is present in the extracted oil at a level of between 1% and 30% of the total fatty acid content,
iv) LA is present in the extracted oil at a level of between 4% and 35% of the total fatty acid content,
v) GLA is present in the extracted oil at a level of less than 4% of the total fatty acid content,
vi) ALA is present in the extracted oil at a level of between 4% and 40% of the total fatty acid content,
vii) the total saturated fatty acid content of the extracted oil is between 4% and 250 of the total fatty acid content,
viii) 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,
ix) myristic acid, if present, is present at a level of less than 1% of the total fatty acid content, and
x) eicosatrienoic acid (ETrA), if present, is present at a level of less than 4% of the total fatty acid content,

thereby producing the ethyl esters.

9. The process of claim 8 , wherein γ-linolenic acid (GLA) is present in the extracted oil at a level of less than 3% of the total fatty acid content.

10. The process of claim 8 , wherein oleic acid is present in the extracted oil at a level of between 6% and 30% of the total fatty acid content.

11. The process of claim 8 , wherein the total saturated fatty acid content of the extracted oil is between 6% and 20% of the total fatty acid content.

12. The process of claim 8 , wherein the extracted oil comprises 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 oil is between 0.1 and 1.

13. The process of claim 8 , wherein the extracted oil comprises tri-DHA TAG (TAG 66:18).

14. The process of claim 8 , wherein at least 80% of the DHA esterified in the form of TAG in the extracted oil is at the sn-1 or sn-3 position of the TAG.

15. A process for producing ethyl esters of polyunsaturated fatty acids, the process comprising transesterifying polyunsaturated fatty acids in triacylglycerols (TAG) in oil extracted from Brassica napus seeds 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, or palmitic acid and myristic acid (C14:0),
c) a total ω6 fatty acid content which comprises linoleic acid (LA) and 7-linolenic acid (GLA),
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) DHA is present in the extracted oil at a level of about 5% of the total fatty acid content, wherein at least 70% of the DHA which is esterified in the form of triacylglycerols (TAG) is esterified at the sn-1 or sn-3 position of the TAG,
ii) palmitic acid is present in the extracted oil at a level of between 2% and 16% of the total fatty acid content,
iii) oleic acid is present in the extracted oil at a level of between 1% and 30% of the total fatty acid content,
iv) LA is present in the extracted oil at a level of between 4% and 35% of the total fatty acid content,
v

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

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P9/06

  Antiarrhythmics · CPC title

• A61P7/02

  Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors · 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

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title