Oil comprising polyunsaturated fatty acids

Patent metadata

Field	Value
Publication number	US-10655082-B2
Application number	US-201815961200-A
Country	US
Kind code	B2
Filing date	Apr 24, 2018
Priority date	Jun 15, 2012
Publication date	May 19, 2020
Grant date	May 19, 2020

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 extracted plant lipid comprising the steps of:
i) obtaining a Brassica napus seed comprising extractable lipid having a total fatty acid content comprising fatty acids in an esterified form, the fatty acids comprising oleic acid, palmitic acid, a total ω6 fatty acid content which comprises linoleic acid (LA) and γ-linolenic acid (GLA), a total ω3 fatty acid content which comprises α-linolenic acid (ALA), stearidonic acid (SDA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA) and eicosatetraenoic acid (ETA), wherein
a) EPA, DPA and DHA, and optionally arachidonic acid (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 extractable lipid is between 7% and 25% of the total fatty acid content,
b) eicosatrienoic acid (ETrA) is present in the extractable lipid at a level of between 0.05% and 3% of the total fatty acid content,
c) palmitic acid is present in the extractable lipid at a level of between 2% and 16% of the total fatty acid content,
d) oleic acid is present in the extractable lipid at a level of between 1% and 30%, or between 30% and 60%, of the total fatty acid content,
e) LA is present in the extractable lipid at a level of between 4% and 35% of the total fatty acid content,
f) GLA is present in the extractable lipid at a level of less than 4% of the total fatty acid content,
g) ALA is present in the extractable lipid at a level of between 2% and 16% of the total fatty acid content,
h) the total saturated fatty acid content of the extractable lipid is between 4% and 25% of the total fatty acid content,
i) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content of the extractable lipid is between 0.1 and 3.0,
j) myristic acid, if present, is present in the extractable lipid at a level of less than 1% of the total fatty acid content, and
k) 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, and

ii) extracting lipid from the Brassica napus seed to thereby produce extracted plant lipid.

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

3. The process of claim 1 , wherein the total saturated fatty acid content of the extractable lipid is between 6% and 20% of the total fatty acid content.

4. The process of claim 1 , wherein the extractable lipid 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.

5. The process of claim 1 , wherein the extractable lipid comprises tri-DHA TAG (TAG 66:18).

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

7. The process 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%.

8. The process 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 75% and 98%.

9. The process of claim 1 , wherein DHA is present in the extractable lipid at a level of about 3% of the total fatty acid content.

10. The process of claim 1 , wherein DHA is present in the extractable lipid at a level of about 4% of the total fatty acid content.

11. The process of claim 1 , wherein DHA is present in the extractable lipid at a level of about 5% of the total fatty acid content.

12. The process of claim 1 , wherein DHA is present in the extractable lipid at a level of about 6% of the total fatty acid content.

13. The process of claim 1 , wherein DHA is present in the extractable lipid at a level of between 7% and 20% of the total fatty acid content.

14. A process for producing extracted plant lipid comprising the steps of:
i) obtaining Brassica napus seeds from Brassica napus plants grown in a field as a population of at least 1,000 plants, which seeds comprise extractable lipid having a total fatty acid content comprising fatty acids in an esterified form, the fatty acids comprising oleic acid, palmitic acid, a total ω6 fatty acid content which comprises linoleic acid (LA) and γ-linolenic acid (GLA), a total ω3 fatty acid content which comprises α-linolenic acid (ALA), stearidonic acid (SDA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA) and eicosatetraenoic acid (ETA), wherein
a) EPA, DPA and DHA, and optionally arachidonic acid (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 extractable lipid is between 7% and 25% of the total fatty acid content,
b) 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,
c) eicosatrienoic acid (ETrA) is present in the extractable lipid at a level of between 0.05% and 3% of the total fatty acid content,
d) palmitic acid is present in the extractable lipid at a level of between 2% and 16% of the total fatty acid content,
e) oleic acid is present in the extractable lipid at a level of between 1% and 30% , or between 30% and 60%, of the total fatty acid content,
f) LA is present in the extractable lipid at a level of between 4% and 35% of the total fatty acid content,
g) GLA is present in the extractable lipid at a level of less than 4% of the total fatty acid content,
h) the total saturated fatty acid content of the extractable lipid is between 4% and 25% of the total fatty acid content,
i) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content of the extractable lipid is between 0.1 and 3.0, and
j) myristic acid, if present, is present in the extractable lipid at a level of less than 1% of the total fatty acid content, and

ii) extracting lipid from the Brassica napus seeds to thereby produce extracted plant lipid.

15. The process of claim 14 , wherein the process comprises, prior to step (i), a step of cultivating the at least 1000 Brassica napus plants in the field, and step (i) comprises harvesting Brassica napus seeds from the at least 1000 Brassica napus plants.

16. A process for producing purified extracted plant lipid, comprising (i) obtaining the extracted plant lipid produced by the process of claim 14 , and (ii) purifying the extracted plant lipid to thereby produce purified extracted plant lipid.

17. A process for producing fatty acid esters, comprising (i) obtaining the purified extracted plant lipid produced by the process of claim 16 , and (ii) transesterifying the purified extracted

Assignees

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

Inventors

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

Classifications

• C11C3/06

  with glycerol · CPC title

• A23K20/158

  Fatty acids; Fats; Products containing oils or fats · CPC title

• C12N15/8234

  Seed-specific, e.g. embryo, endosperm · 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

• A61K31/232 Primary

  having three or more double bonds, e.g. etretinate · CPC title