Process for producing ethyl esters of polyunsaturated fatty acids

Patent metadata

Field	Value
Publication number	US-9932289-B2
Application number	US-201715400532-A
Country	US
Kind code	B2
Filing date	Jan 6, 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

The invention claimed is:

1. A process for producing polyunsaturated fatty acids in an esterified form, the process comprising transesterifying polyunsaturated fatty acids in canola seedoil, wherein the canola seedoil comprises a total fatty acid content which comprises docosahexaenoic acid (DHA, 22:6ω3), wherein the DHA is present at a level of between 7% and 20% of the total fatty acid content, and wherein at least 70% of the DHA in the total fatty acid content is esterified at an sn-1 or sn-3 position of triacylglycerol (TAG) in the canola seedoil.

2. The process of claim 1 , wherein the canola seedoil comprises docosapentaenoic acid (DPA, 22:5ω3), wherein the DPA is present at a level of less than 4% of the total fatty acid content.

3. The process of claim 1 , comprising a total saturated fatty acid content which comprises palmitic acid, or palmitic acid and myristic acid (C14:0), wherein the palmitic acid is present at a level of between 2% and 16% of the total fatty acid content and the myristic acid, if present, is present at a level of less than 1% of the total fatty acid content.

4. The process of claim 1 , wherein a sum total of arachidonic acid (ARA), eicosapentaenoic acid (EPA), DPA and DHA is present in the canola seedoil of between 7% and 25% of the total fatty acid content.

5. The process of claim 1 which has one or more or all of the following features
i) a level of γ-linolenic acid (GLA) of less than 4% is present in the total fatty acid content of the canola seedoil,
ii) a level of stearidonic acid (SDA) of less than 4% is present in the total fatty acid content of the canola seedoil,
iii) a level of eicosatetraenoic acid (ETA) of less than 4% is present in the total fatty acid content of the canola seedoil,
iv) a level of eicosatrienoic acid (ETrA) between 0.05% and 2% is present in the total fatty acid content of the canola seedoil,
v) a level of EPA of less than 10% is present in the total fatty acid content of the canola seedoil,
vi) a level of total saturated fatty acid between 4% and 25% is present in the total fatty acid content of the canola seedoil,
vii) a total monounsaturated fatty acid content of between 4% and 35% is present in the total fatty acid content of the canola seedoil,
viii) the canola seedoil comprises new ω6 fatty acids in the total ω6 fatty acid content, wherein the level of new ω6 fatty acids in the canola seedoil is between 0.5% and 10% of the total fatty acid content,
ix) a total ω3 fatty acid content is present in the canola seedoil of between 10% and about 20% of the total fatty acid content,
x) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content in the canola seedoil is between 0.05 and 3.0,
xi) the canola seedoil 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 fatty acid content of the canola seedoil is between 0.03 and 3.0,
xii) the canola seedoil has a fatty acid composition based on an efficiency of conversion of oleic acid to DHA of at least 10%,
xiii) the canola seedoil has a fatty acid composition based on an efficiency of conversion of LA to DHA of at least 15%,
xiv) the canola seedoil has a fatty acid composition based on an efficiency of conversion of ALA to DHA of at least 17%,
xv) the total fatty acid content in the canola seedoil has less than 1% C20:1, and
xvi) at least 80% of the total fatty acid content of the canola seedoil is esterified in the form of TAG.

6. The process of claim 1 , comprising one or more or all of campesterol, Δ5-stigmasterol, eburicol, β-sitosterol, Δ5-avenasterol, Δ7-stigmasterol and Δ7-avenasterol.

7. The process of claim 1 , wherein a level of α-linolenic acid (ALA) between 2% and 16% is present in the total fatty acid content of the canola seedoil.

8. The process of claim 1 , wherein a level of GLA of less than 4% is present in the total fatty acid content of the canola seedoil.

9. The process of claim 1 , wherein a level of SDA between 0.05% and 7% is present in the total fatty acid content of the canola seedoil.

10. The process of claim 1 , wherein a level of ETA between 0.05% and 4% is present in the total fatty acid content of the canola seedoil.

11. The process of claim 1 , wherein a level of DPA between 0.05% and 8% is present in the total fatty acid content of the canola seedoil.

12. The process of claim 3 , wherein the total saturated fatty acid content in the canola seedoil is between 4% and 20% of the total fatty acid content.

13. The process of claim 1 , wherein a total monounsaturated fatty acid content of between 4% and 35% is present in the total fatty acid content of the canola seedoil.

14. The process of claim 1 , comprising a total polyunsaturated fatty acid content of between 20% and 75% of the total fatty acid content.

15. The process of claim 1 , comprising new ω3 fatty acids in a total ω3 fatty acid content, wherein the level of new ω3 fatty acids in the canola seedoil is between 9% and 33% of the total fatty acid content.

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

17. The process of claim 1 , wherein the canola seedoil comprises tri-DHA TAG (TAG 66:18).

18. The process of claim 1 , wherein a level of about 1% C20:1 is present in the total fatty acid content in the canola seedoil.

Assignees

• Commw Scient Ind Res Org
• Grains Res & Dev Corp
• Nuseed Pty Ltd
• Commonwealth Scient And Industrial Research Ogranisation
• 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

• A61P9/06

  Antiarrhythmics · CPC title

• A61P7/02

  Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors · CPC title

• A61P9/12

  Antihypertensives · 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