IP Library Granted Patent US 11,834,621
Granted Patent B2
US 11,834,621 · App. 17/150,898 · Granted Dec 5, 2023

Lipid comprising polyunsaturated fatty acids

Inventors: James Robertson Petrie (Goulburn, AU); Surinder Pal Singh (Downer, AU); Robert Charles de Feyter (Monash, AU)
Assignee: NUSEED GLOBAL INNOVATION LTD.
C11B1/10A01H1/104A01H5/10A01H6/20A61K36/31C07C57/02C07C57/03C07C67/02C11B1/00C11C1/002C11C3/00C11C3/003C11C3/06C12N9/1025C12N15/8247A23K20/158A23L33/12A23V2002/00A61K31/231A61K31/232A61K2236/35C07K14/415
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Quick Facts
Patent No.
US 11,834,621
App. No.
17/150,898
Granted
Dec 5, 2023
Kind
B2
Abstract

The present invention relates to extracted plant lipid, comprising fatty acids in an esterified form.

Claims (62)

1. A process for producing ethyl esters of polyunsaturated fatty acids, the process comprising transesterifying triacylglycerols in Brassica napus seedoil to thereby produce the ethyl esters, wherein the Brassica napus seedoil comprises fatty acids esterified in the form of triacylglycerols, the fatty acids comprising

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) palmitic acid is present at a level of between 2% and 16% of the total fatty acid content of the Brassica napus seedoil,

ii) oleic acid is present at a level of between 1% and 60% of the total fatty acid content of the Brassica napus seedoil,

iii) LA is present at a level of between 4% and 35% of the total fatty acid content of the Brassica napus seedoil,

iv) GLA is present at a level of less than 4% of the total fatty acid content of the Brassica napus seedoil,

v) ALA is present at a level of between 2% and 16% of the total fatty acid content of the Brassica napus seedoil,

vi) the total saturated fatty acid content is between 4% and 25% of the total fatty acid content of the Brassica napus seedoil,

vii) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content in the total fatty acid content of the Brassica napus seedoil is between 0.05 and 3.0,

viii) myristic acid is present at a level of less than 2% of the total fatty acid content of the Brassica napus seedoil or is absent,

ix) eicosatrienoic acid (ETrA) is present at a level of less than 4% of the total fatty acid content of the Brassica napus seedoil or is absent, and

x) 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,

wherein the level or content percentages correspond to a percentage by weight.

2. The process of claim 1 , wherein the total saturated fatty acid content of the Brassica napus seedoil is between 6% and 20% of the total fatty acid content of the Brassica napus seedoil.

3. The process of claim 1 , wherein the total fatty acid content of the Brassica napus 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 Brassica napus seedoil is between 0.03 and 3.0.

4. The process of claim 1 , wherein the Brassica napus seedoil comprises new ω3 fatty acids in the total ω3 fatty acid content, the new ω3 fatty acids comprising the SDA, ETA, EPA, DPA and DHA, and wherein the level of new ω3 fatty acids in the Brassica napus seedoil is between 10% and 20% of the total fatty acid content by weight.

5. A process for producing ethyl esters of polyunsaturated fatty acids, the process comprising transesterifying triacylglycerols in Brassica napus seedoil to thereby produce the ethyl esters, wherein the Brassica napus seedoil comprises fatty acids esterified in the form of triacylglycerols, the fatty acids comprising

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) palmitic acid is present at a level of between 2% and 16% of the total fatty acid content of the Brassica napus seedoil,

ii) oleic acid is present at a level of between 1% and 60% of the total fatty acid content of the Brassica napus seedoil,

iii) LA is present at a level of between 4% and 35% of the total fatty acid content of the Brassica napus seedoil,

iv) GLA is present at a level of less than 4% of the total fatty acid content of the Brassica napus seedoil,

v) the total saturated fatty acid content is between 4% and 25% of the total fatty acid content of the Brassica napus seedoil,

vi) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content in the total fatty acid content of the Brassica napus seedoil is between 0.05 and 3.0,

vii) myristic acid is present at a level of less than 2% of the total fatty acid content of the Brassica napus seedoil or is absent,

viii) eicosatrienoic acid (ETrA) is present at a level of less than 4% of the total fatty acid content of the Brassica napus seedoil or is absent, and

ix) 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,

wherein the level or content percentages correspond to a percentage by weight.

6. The process of claim 5 , wherein the Brassica napus seedoil comprises new ω3 fatty acids in the total ω3 fatty acid content, the new ω3 fatty acids comprising the SDA, ETA, EPA, DPA and DHA, and wherein the level of new ω3 fatty acids in the Brassica napus seedoil is between 10% and 20% of the total fatty acid content by weight.

7. A process for producing ethyl esters of polyunsaturated fatty acids, the process comprising transesterifying triacylglycerols in Brassica napus seedoil to thereby produce the ethyl esters, wherein the Brassica napus seedoil comprises fatty acids esterified in the form of triacylglycerols, the fatty acids comprising

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) palmitic acid is present at a level of between 2% and 16% of the total fatty acid content of the Brassica napus seedoil,

ii) oleic acid is present at a level of 27-33% of the total fatty acid content of the Brassica napus seedoil,

iii) LA is present at a level of between 4% and 35% of the total fatty acid content of the Brassica napus seedoil,

iv) GLA is present at a level of less than 4% of the total fatty acid content of the Brassica napus seedoil,

v) the total saturated fatty acid content is between 4% and 25% of the total fatty acid content of the Brassica napus seedoil,

vi) myristic acid is present at a level of less than 2% of the total fatty acid content of the Brassica napus seedoil or is absent,

vii) eicosatrienoic acid (ETrA) is present at a level of less than 4% of the total fatty acid content of the Brassica napus seedoil or is absent, and

viii) 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,

wherein the level or content percentages correspond to a percentage by weight.

8. The process of claim 7 , wherein the Brassica napus seedoil comprises new ω3 fatty acids in the total ω3 fatty acid content, the new ω3 fatty acids comprising the SDA, ETA, EPA, DPA and DHA, and wherein the level of new ω3 fatty acids in the Brassica napus seedoil is between 10% and 20% of the total fatty acid content by weight.

9. The process of claim 1 , wherein at least 80% of the DHA esterified in the form of TAG in the total fatty acid content of the Brassica napus seedoil is at the sn-1 or sn-3 position of the TAG.

10. The process of claim 4 , wherein at least 80% of the DHA esterified in the form of TAG in the total fatty acid content of the Brassica napus seedoil is at the sn-1 or sn-3 position of the TAG.

11. The process of claim 5 , wherein at least 80% of the DHA esterified in the form of TAG in the total fatty acid content of the Brassica napus seedoil is at the sn-1 or sn-3 position of the TAG.

12. The process of claim 6 , wherein at least 80% of the DHA esterified in the form of TAG in the total fatty acid content of the Brassica napus seedoil is at the sn-1 or sn-3 position of the TAG.

13. The process of claim 7 , wherein at least 80% of the DHA esterified in the form of TAG in the total fatty acid content of the Brassica napus seedoil is at the sn-1 or sn-3 position of the TAG.

14. The process of claim 8 , wherein at least 80% of the DHA esterified in the form of TAG in the total fatty acid content of the Brassica napus seedoil is at the sn-1 or sn-3 position of the TAG.

15. The process of claim 1 , further comprising a step of fractionation or distillation of the ethyl esters to increase the level of DHA.

16. The process of claim 5 , further comprising a step of fractionation or distillation of the ethyl esters to increase the level of DHA.

17. The process of claim 7 , further comprising a step of fractionation or distillation of the ethyl esters to increase the level of DHA.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2022
From: NUSEED PROPRIETARY LIMITED
To: NUSEED NUTRITIONAL AUSTRALIA PTY LTD
Reel/Frame 059669/0648 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2022
From: PETRIE, JAMES ROBERTSON; SINGH, SURINDER PAL; DE FEYTER, ROBERT CHARLES
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 059417/0037 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2022
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED PTY LTD
Reel/Frame 060206/0678 →
Continuity (9)
Continuation 15975497 · May 9, 2018
Continuation 15373145 · Dec 8, 2016
Continuation 14464510 · Aug 20, 2014
Continuation 13918399 · Jun 14, 2013
Provisional Application 61782680 · Mar 14, 2013
Provisional Application 61697676 · Sep 6, 2012
Provisional Application 61663344 · Jun 22, 2012
Provisional Application 61660392 · Jun 15, 2012
Related Publication 20210139809A1 · May 13, 2021