Process for producing polyunsaturated fatty acids in an esterified form
The present invention relates to a process for producing ethyl esters of polyunsaturated fatty acids, comprising transesterifying triacylglycerols in extracted plant lipid.
1. A process for producing polyunsaturated fatty acids in an esterified form, the process comprising hydrolyzing or transesterifying the polyunsaturated fatty acids in triacylglycerols (TAG) in extracted plant lipid whose total fatty acid content 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),
(d) a total ω3 fatty acid content which comprises α-linolenic acid (ALA), docosahexaenoic acid (DHA) and one or more of stearidonic acid (SDA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA) and eicosatetraenoic acid (ETA),
(e) less than 1% myristic acid (C14:0), and
(f) less than 4% eicosatrienoic acid (ETrA),
wherein
(i) a level of DHA of between 7% and 20% is present in the total fatty acid content of the extracted plant lipid, wherein at least 70% of the DHA is esterified at the sn-1 or sn-3 position of the TAG,
(ii) a level of palmitic acid between 2% and 16% is present in the total fatty acid content of the extracted plant lipid,
(iii) a level of oleic acid between 1% and 60% is present in the total fatty acid content of the extracted plant lipid,
(iv) a level of linoleic acid (LA) between 4% and 35% is present in the total fatty acid content of the extracted plant lipid,
(v) a level of α-linolenic acid (ALA) between 4% and 40% is present in the total fatty acid content of the extracted plant lipid,
(vi) the total saturated fatty acid content of the extracted plant lipid is between 4% and 25% of the total ratty acid content,
(vii) the ratio of the total ω6 fatty acid content to the total ω3fatty acid content of the extracted plant lipid is between 0.1 and 3.0, and
(viii) at least 70% of the total fatty acid content of the extracted plant lipid is esterified in the form of TAG, thereby producing the polyunsaturated fatty acids in an esterified form.
2. The process of claim 1 in which the extracted plant lipid has one or more or all of the following features
i) a level of palmitic acid between 2% and 15% is present in the total fatty acid content of the extracted plant lipid,
ii) a level of oleic acid between about 3% and about 30%, is present in the total fatty acid content of the extracted plant lipid,
iii) a level of linoleic acid (LA) between 4% and about 20% is present in the total fatty acid content of the extracted plant lipid,
iv) a level of α-linolenic acid (ALA) between about 10% and about 35% is present in the total fatty acid content of the extracted plant lipid,
v) a level of γ-linolenic acid (GLA) less than 4% is present in the total fatty acid content of the extracted plant lipid,
vi) a level of stearidonic acid (SDA) between 0.05% and about 7% is present in the total fatty acid content of the extracted plant lipid,
vii) a level of eicosatetraenoic acid (ETA) between 0.05% and about 4% is present in the total fatty acid content of the extracted plant lipid,
viii) a level of eicosatrienoic acid (ETrA) between 0.05% and about 2% is present in the total fatty acid content of the extracted plant lipid,
ix) the extracted plant lipid comprises ω6-docosapentaenoic acid (22:5 Δ4,7,10,13,16 ) in its total fatty acid content,
x) a level of SDA of less than about 0.1%, EPA of less than about 0.1% and ETA of less than about 0.1% in its total fatty acid content,
xi) the total saturated fatty acid content in the extracted plant lipid is between about 4% and about 20% of the total fatty acid content,
xii) the total monounsaturated fatty acid content in the extracted plant lipid is between about 4% and about 35% of the total fatty acid content,
xiii) the extracted plant lipid comprises a total polyunsaturated fatty acid content comprising the total ω6 fatty acid content and the total ω3 fatty acid content, wherein the total polyunsaturated fatty acid content in the extracted plant lipid is between about 20% and about 75% of the total fatty acid content,
xiv) the total ω6 fatty acid content in the extracted plant lipid is less than 20% of the total fatty acid content,
xv) the extracted plant lipid comprises new ω6 fatty acids in the total ω6 fatty acid content, wherein the level of new ω6 fatty acids in the extracted plant lipid is less than about 10% of the total fatty acid content,
xvi) the total ω3 fatty acid content in the extracted plant lipid is between 36% and about 65% of the total fatty acid content,
xvii) the extracted plant lipid comprises new ω3 fatty acids in the total ω3 fatty acid content, wherein the level of new ω3 fatty acids in the extracted plant lipid is between 9% and about 33% of the total fatty acid content,
xviii) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content in the extracted plant lipid is between about 0.1 and about 0.5,
xix) the extracted plant 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 plant lipid is between about 0.1 and about 1,
xx) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of oleic acid to DHA of at least about 10%,
xxi) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of LA to DHA of at least about 15%,
xxii) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of ALA to DHA of at least about 17%,
xxiii) the total fatty acid content in the extracted plant lipid has less than 1% C20:1,
xxiv) at least about 80% of the total fatty acid content of the extracted plant lipid is esterified in the form of TAG,
xxv) the extracted plant lipid comprises diacylglycerol (DAG),
xxvi) the extracted plant lipid comprises less than about 10% free (non-esterified) fatty acids and/or phospholipid, and
xxvii) the extracted plant lipid comprises tri-DHA TAG (TAG 66:18).
3. The process of claim 1 , wherein the extracted plant lipid is in the form of an oil, and wherein the oil comprises one or more sterols.
4. The process of claim 3 , wherein the oil comprises less than 10 mg of sterols/g of oil.
5. The process of claim 3 , wherein the oil comprises one or more or all of campesterol, Δ5-stigmasterol, eburicol, β-sitosterol, Δ5-avenasterol, Δ7-stigmasterol, and Δ7-avenasterol.
6. The process of claim 3 , wherein the oil has a level of cholesterol of less than about 0.5% by weight.
7. The process of claim 1 , wherein the extracted plant lipid is in the form of an oil from an oilseed.
8. The process of claim 7 , wherein the oilseed is a Brassica sp. oilseed or a Camelina sativa oilseed.
9. The process of claim 7 , wherein the oilseed is canola seed.
10. The process of claim 8 in which the extracted plant lipid has one or more or all of the following features
i) a level of palmitic acid between 2% and 15% is present in the total fatty acid content of the extracted plant lipid,
ii) a level of oleic acid between about 3% and about 30% is present in the total fatty acid content of the extracted plant lipid,
iii) a level of linoleic acid (LA) between 4% and about 20% is present in the total fatty acid content of the extracted plant lipid,
iv) a level of α-linolenic acid (ALA) is present in the total fatty acid content of the extracted plant lipid,
v) a level of γ-linolenic acid (GLA) less than 4% is present in the total fatty acid content of the extracted plant lipid,
vi) a level of stearidonic acid (SDA) between 0.05% and about 4% is present in the total fatty acid content of the extracted plant lipid,
vii) a level of eicosatetraenoic acid (ETA) between 0.05% and about 4% is present in the total fatty acid content of the extracted plant lipid,
viii) a level of eicosatrienoic acid (ETτA) between 0.05% and about 2% is present in the total fatty acid content of the extracted plant lipid,
ix) the extracted plant lipid comprises ω6-docosapentaenoic acid (22:5 Δ4,7,10,13,16 ) in its total fatty acid content,
x) a level of SDA of less than about 0.1%, EPA of less than about 0.1% and ETA of less than about 0.1% in its total fatty acid content,
xi) the total saturated fatty acid content in the extracted plant lipid is between about 4% and about 20% of the total fatty acid content,
xii) the total monounsaturated fatty acid content in the extracted plant lipid is between about 4% and about 35% of the total fatty acid content,
xiii) the extracted plant lipid comprises a total polyunsaturated fatty acid content comprising the total ω6 fatty acid content and the total ω3 fatty acid content, wherein the total polyunsaturated fatty acid content in the extracted plant lipid is between about 20% and about 75% of the total fatty acid content,
xiv) the total ω6 fatty acid content in the extracted plant lipid is less than 20% of the total fatty acid content,
xi) the extracted plant lipid comprises new ω6 fatty acids in the total ω6 fatty acid content, wherein the level of new ω6 fatty acids in the extracted plant lipid is less than about 10% of the total fatty acid content,
xvi) the total ω3 fatty acid content in the extracted plant lipid is between 36% and about 65% of the total fatty acid content,
xvii) the extracted plant lipid comprises new ω3 fatty acids in the total ω3 fatty acid content, wherein the level of new ω3 fatty acids in the extracted plant lipid is between 9% and about 33% of the total fatty acid content,
xviii) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content in the extracted plant lipid is between about 0.1 and about 0.5,
xix) the extracted plant 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 plant lipid is between about 0.1 and about 1,
xx) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of oleic acid to DHA of at least about 10%,
xxi) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of LA to DHA of at least about 15%,
xxii) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of ALA to DHA of at least about 17%,
xxiii) the total fatty acid content in the extracted plant lipid has less than 1% C20:1,
xxiv) at least about 80% of the total fatty acid content of the extracted plant lipid is esterified in the form of TAG,
xxv) the extracted plant lipid comprises diacylglycerol (DAG),
xxvi) the extracted plant lipid comprises less than about 10% free (non-esterified) fatty acids and/or phospholipid, and
xxvii) the extracted plant lipid comprises tri-DHA TAG (TAG 66:18).
11. The process of claim 8 , wherein the oil comprises less than 10 mg of sterols/g of oil.
12. The process of claim 8 , wherein the oil comprises one or more or all of campesterol, Δ5-stigmasterol, eburicol, β-sitosterol, Δ5-avenasterol, Δ7-stigmasterol, and Δ7-avenasterol.
13. The process of claim 8 , wherein the oil has a level of cholesterol of less than about 0.5% by weight.
14. The process of claim 1 , wherein the polyunsaturated fatty acids in an esterified form are ethyl esters of the polyunsaturated fatty acids.
15. The process of claim 14 in which the extracted plant lipid has one or more or all of the following features
i) a level of palmitic acid between 2% and 15% is present in the total fatty acid content of the extracted plant lipid,
ii) a level of oleic acid between about 3% and about 30% is present in the total fatty acid content of the extracted plant lipid,
iii) a level of linoleic acid (LA) between 4% and about 20% is present in the total fatty acid content of the extracted plant lipid,
iv) a level of α-linolenic acid (ALA) between about 10% and about 35% is present in the total fatty acid content of the extracted plant lipid,
v) a level of γ-linolenic acid (GLA) less than 4% is present in the total fatty acid content of the extracted plant lipid,
vi) a level of stearidonic acid (IDA) between 0.05% and about 4% is present in the total fatty acid content of the extracted plant lipid,
vii) a level of eicosatetraenoic acid (ETA) between 0.05% and about 4% is present in the total fatty acid content of the extracted plant lipid,
viii) a level of eicosatrienoic acid (ETrA) between 0.05% and about 2% is present in the total fatty acid content of the extracted plant lipid,
ix) the extracted plant lipid comprises ω6-docosapentaenoic acid (22:5 Δ4,7,10,13,16 ) in its total fatty acid content,
x) a level of IDA of less than about 0.1%, EPA of less than about 0.1% and ETA of less than about 0.1% in its total fatty acid content,
xi) the total saturated fatty acid content in the extracted plant lipid is between about 4% and about 20% of the total fatty acid content,
xii) the total monounsaturated fatty acid content in the extracted plant lipid is between about 4% and about 35% of the total fatty acid content,
xiii) the extracted plant lipid comprises a total polyunsaturated fatty acid content comprising the total ω6 fatty acid content and the total ω3 fatty acid content, wherein the total polyunsaturated fatty acid content in the extracted plant lipid is between about 20% and about 75% of the total fatty acid content,
xiv) the total ω6 fatty acid content in the extracted plant lipid is less than 20% of the total fatty acid content,
xv) the extracted plant lipid comprises new ω6 fatty acids in the total (16 fatty acid content, wherein the level of new ω6 fatty acids in the extracted plant lipid is less than about 10% of the total fatty acid content,
xvi) the total ω3 fatty acid content in the extracted plant lipid is between 36% and about 65% of the total fatty acid content,
xvii) the extracted plant lipid comprises new ω3 fatty acids in the total ω3 fatty acid content, wherein the level of new ω3 fatty acids in the extracted plant lipid is between 9% and about 33% of the total fatty acid content,
xviii) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content in the extracted plant lipid is between about 0.1 and about 0.5,
xix) the extracted plant 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 plant lipid is between about 0.1 and about 1,
xx) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of oleic acid to DHA of at least about 10%,
xxi) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of LA to DHA of at least about 15%,
xxii) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of ALA to DHA of at least about 17%,
xxiii) the total fatty acid content in the extracted plant lipid has less than 1% C20:1,
xxiv) at least about 80% of the total fatty acid content of the extracted plant lipid is esterified in the form of TAG,
xxv) the extracted plant lipid comprises diacylglycerol (DAG), and
xxvi) the extracted plant lipid comprises less than about 10% free (non-esterified) fatty acids and/or phospholipid, and
xxvii) the extracted plant lipid comprises tri-DHA TAG (TAG 66:18).
16. The process of claim 14 , wherein the extracted plant lipid is in the form of an oil, and wherein the oil comprises one or more sterols.
17. The process of claim 16 , wherein the oil comprises less than 10 mg of sterols/g of oil.
18. The process of claim 16 , wherein the oil comprises one or more or all of campesterol, Δ5-stigmasterol, eburicol, β-sitosterol, Δ5-avenasterol, Δ7-stigmasterol, and Δ7-avenasterol.
19. The process of claim 16 , wherein the oil has a level of cholesterol of less than about 0.5% by weight.
20. The process of claim 14 , wherein the extracted plant lipid is in the form of an oil from an oilseed.
21. The process of claim 20 , wherein the oilseed is a Brassica sp. oilseed or a Camelina sativa oilseed.
22. The process of claim 1 , wherein a level of eicosapentaenoic acid (EPA) of less than 4% is present in the total fatty acid content of the extracted plant lipid.
23. The process of claim 1 , wherein a level of docosapentaenoic acid (DPA) of between 0.05% and 8% is present in the total fatty acid content of the extracted plant lipid.
24. The process of claim 1 , wherein the extracted plant lipid comprises less than 0.1% ω6-docosapentaenoic acid (22:5 Δ4,7,10,13,16 ) in its fatty acid content.
25. The process 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.
26. The process of claim 1 , wherein the most abundant DHA-containing TAG species in the extracted plant lipid is DHA/18:3/18:3 (TAG 58:12).
27. The process of claim 1 , wherein a level of docosahexaenoic acid (DHA) of between 8% and 20% is present in the total fatty acid content of the extracted plant lipid.
28. The process of claim 1 , wherein a level of docosahexaenoic acid (DHA) of between 10% and 20% is present in the total fatty acid content of the extracted plant lipid.
29. The process of claim 1 , wherein level of docosahexaenoic acid (DHA) of between 11% and 20% is present in the total fatty acid content of the extracted plant lipid.
30. A process for producing polyunsaturated fatty acids in an esterified form, the process comprising hydrolyzing or transesterifying the polyunsaturated fatty acids in triacylglycerols (TAG) in extracted plant lipid whose total fatty acid content 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 ad (LA),
(d) a total ω3 fatty acid content which comprises e linolenic acid (ALA) and docosahexaenoic acid (DHA),
(e) less than 1% myristic acid (G14:0), and
(f) less than 4% eicosatrienoic acid (ETrA),
wherein
(i) a level of DHA of about 3%, about 4%, about 5% or about 6% is present in the total fatty acid content of the extracted plant lipid, wherein at least 70% of the DHA is esterified at the sn-1 or sn-3 position of the TAG,
(ii) a level of palmitic acid between 2% and 16% is present in the total fatty acid content of the extracted plant lipid,
(iii) a level of oleic acid between 1% and 60% is present in the total fatty acid content of the extracted plant lipid,
(iv) a level of linoleic acid (LA) between 4% and 35% is present in the total fatty acid content of the extracted plant lipid,
(v) a level of α-linolenic acid (ALA) between 4% and 40% is present in the total fatty acid content of the extracted plant lipid,
(vi) the total saturated fatty acid content of the extracted plant lipid is between 4% and 25% of the total fatty acid content,
(vii) the ratio of the total ω6 fatty acid content to the total ω3fatty acid content of the extracted plant lipid is between 0.1 and 3.0, and
(viii) at least 70% of the total fatty acid content of the extracted plant lipid is esterified at the form of TAG, thereby producing the polyunsaturated fatty acids in an esterified form.
31. The process of claim 30 in which the extracted plant lipid has one or more or all of the following features
i) a level of palmitic acid between 2% and 15% is present in the total fatty acid content of the extracted plant lipid,
ii) a level of oleic acid between about 3% and about 30% is present in the total fatty acid content of the extracted plant lipid,
iii) a level of linoleic acid (LA) between about 4% and about 20% is present in the total fatty acid content of the extracted plant lipid,
iv) a level of α-linolenic acid (ALA) between about 10% and about 35% is present in the total fatty acid content of the extracted plant lipid,
v) a level of γ-linolenic acid (GLA) less than 4% is present in the total fatty acid content of the extracted plant lipid,
vi) a level of stearidonic acid (SDA) between 0.05% and about 7% is present in the total fatty acid content of the extracted plant lipid,
vii) a level of eicosatetraenoic acid (ETA) between 0.05% and about 4% is present in the total fatty acid content of the extracted plant lipid,
viii) a level of eicosatrienoic acid (ETrA) between 0.05% and about 2% is present in the total fatty acid content of the extracted plant lipid,
ix) the extracted plant lipid comprises ω6-docosapentaenoic acid (22:5 66 4,7,10,13,16 ) in its total fatty acid content,
x) a level of SDA of less than about 0.1%, EPA of less than about 0.1% and ETA of less than about 0.1% in its total fatty acid content,
xi) the total saturated fatty acid content in the extracted plant lipid is between about 4% and about 20% of the total fatty acid content,
xii) the total monounsaturated fatty acid content in the extracted plant lipid is between about 4% and about 35% of the total fatty acid content,
xiii) the extracted plant lipid comprises a total polyunsaturated fatty acid content comprising the total ω6 fatty acid content and the total ω3 fatty acid content, wherein the total polyunsaturated fatty acid content in the extracted plant lipid is between about 20% and about 75% of the total fatty acid content,
xiv) the total ω6 fatty acid content in the extracted plant lipid is less than 20% of the total fatty acid content,
xv) the extracted plant lipid comprises new ω6 fatty acids in the total ω6 fatty acid content, wherein the level of new ω6 fatty acids in the extracted plant lipid is less than about 10% of the total fatty acid content,
xvi) the total ω3 fatty acid content in the extracted plant lipid is between 36% and about 65% of the total fatty acid content,
xvii) the extracted plant lipid comprises new ω3 fatty acids in the total ω3 fatty acid content, wherein the level of new ω3 fatty acids in the extracted plant lipid is between 9% and about 33% of the total fatty acid content,
xviii) the ratio of the total ω6 fatty acid content to the total ω3fatty acid content in the extracted plant lipid is between about 0.1and about 0.5,
xix) the extracted plant 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 ω6fatty acids to the new ω3 fatty acids in the extracted plant lipid is between about 0.1 and about 1,
xx) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of oleic acid to DHA of at least about 10%,
xxi) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of LA to DHA of at least about 15%,
xxii) the extracted plant lipid has a fatty acid composition based on an efficiency of conversion of ALA to DHA of at least about 17%,
xxiii) the total fatty acid content in the extracted plant lipid has less than 1% C20:1,
xxiv) at least about 80% of the total fatty acid content of the extracted plant lipid is esterified in the form of TAG,
xxv) the extracted plant lipid comprises diacylglycerol (DAG),
xxvi) the extracted plant lipid comprises less than about 10% free (non-esterified) fatty acids and/or phospholipid, and
xxvii) the extracted plant lipid comprises tri-DHA TAG (TAG 66:18).
32. The process of claim 30 , wherein the extracted plant lipid is in the form of an oil, and wherein the oil comprises one or more sterols.
33. The process of claim 32 , wherein the oil comprises less than 10 mg of sterols/g of oil.
34. The process of claim 32 , wherein the oil comprises one or more or all of campesterol, Δ5-stigmasterol, eburicol, β-sitosterol, Δ5-avenasterol, Δ7-stigmasterol, and Δ7-avenasterol.
35. The process of claim 32 , wherein the oil is has a level of cholesterol of less than about 0.5% by weight.
36. The process of claim 30 , wherein the extracted plant lipid is in the form of an oil from an oilseed.
37. The process of claim 36 , wherein the oilseed is a Brassica sp oilseed or a Camelina sativa oilseed.
38. The process of claim 36 , wherein the oilseed is canola seed.
39. The process of claim 30 , wherein a level of oleic acid between 30% and 60% is present in the total fatty acid content of the extracted plant lipid.
40. The process of claim 30 , wherein the polyunsaturated fatty acids in an esterified form are ethyl esters of the polyunsaturated fatty acids.
41. The process of claim 40 , wherein a level of oleic acid between 30% and 60% is present in the total fatty acid content of the extracted plant lipid.
42. The process of claim 1 which comprises transesterifying the polyunsaturated fatty acids in TAG in the extracted plant lipid.
43. The process of claim 30 which comprises transesterifying the polyunsaturated fatty acids in TAG in the extracted plant lipid.