VEGETABLE OIL COMPRISING A POLYUNSATURATED FATTY ACID HAVING AT LEAST 20 CARBON ATOMS

Abstract

The present invention describes a vegetable oil comprising a polyunsatured fatty acid having at least 20 carbon atoms (LC-PUFA), which oil has (a) an anisidine value (AnV) of less than 25; (b) a peroxide value (POV) of less than 10; (c) a triglyceride content of greater than 90%; and/or (d) an Oil Stability Index (OSI) of greater than 5 hours at 80° C.

Claims

1-16. (canceled)

17. Process for obtaining a polyunsaturated fatty acid having at least 20 carbon atoms (LC-PUFA) or an oil comprising a LC-PUFA from seeds, said process comprising (A) one or more or all of (i) to (vi): (i) providing seeds comprising a LC-PUFA and/or an oil comprising a LC-PUFA, (ii) drying the seeds (iii) storing the seeds (iv) grinding and/or flaking the seeds (v) heating the seeds (vi) pressing the seeds such as to expell a fraction of oil And, (B) obtaining the LC-PUFA or oil comprising the LC-PUFA from the seeds, optionally by extraction with a solvent.

18. Process according to claim 17, wherein, e.g. in one or more of (i) to (vi) less than 5% of the seeds are total damaged seeds; less than 2% of the seeds are distinctly green seeds; and/or less than 0.1% of the seeds are heated seeds, as determined in accordance with the Official Grain Grading Guide. 2001 of the Canadian Grain Commission

19. Seeds, comprising a LC-PUFA, of which less than 5% of the seeds are total damaged seeds; less than 2% of the seeds are distinctly green seeds; and/or less than 0.1% of the seeds are heated seeds, as determined in accordance with the Official Grain Grading Guide. 2001 of the Canadian Grain Commission (for Canola and Rapeseed)

20. Process according to claim 17, wherein (ii) comprises drying the seeds at a temperature of below 40° C.

21. Process according to claim 17, wherein (ii) comprises drying the seeds using a fluid bed dryer.

22. Process according to claim 17, wherein (ii) comprises drying the seeds using conditioned air, which preferably has a dew point of <15° C.

23. Process according to claim 17, wherein (ii) comprises drying the seeds, resulting in a moisture content between 6 and 12 wt. %.

24. Process for drying seeds comprising a LC-PUFA, said process comprising drying the seeds as defined in claim 20.

25. Seeds, obtainable by the process according to claim 24.

26. Process according to claim 17, wherein (iii) comprises storing the seeds at a temperature of below 10° C.

27. Process for storing seeds comprising a LC-PUFA, said process comprising storing the seeds at a temperature of below 10° C.

28. Process according to claim 17, wherein (v) comprises heating the seeds, whereby the temperature passes from 40 to 100° C. in less than 1 minute.

29. Process according to claim 17, wherein (v) comprises maintaining the temperature between 120-160° C. for less than 5 minutes.

30. Process according to claim 17, wherein (vi) comprises pressing the seeds to expell oil using a press, for instance a screw press, which is cooled.

31. Process according to claim 17, wherein (vi) comprises pressing the seeds to expell the oil, resulting in pressed oil and a press cake, and wherein B comprises obtaining oil from the press cake by solvent extraction.

32. Process according to claim 17, wherein the seeds are obtained from a transgenic plant.

33. Process according to claim 17, wherein the process further comprises purifying the oil.

34. Process according to claim 33, wherein said purifying comprises deodorizing the oil at a temperature of below 200° C., preferably below 190° C., preferably below 185° C.

35. Process for purifying a vegetable oil comprising an LC-PUFA, said process comprising deodorizing the oil at a temperature of below 200° C., preferably below 190° C., preferably below 185° C.

36. (canceled)

37. Process according to claim 17, wherein the LC-PUFA is an ω-3 or ω-6 PUFA.

38. (canceled)

39. A food product for humans or animals, comprising an oil obtained by a process according to claim 17.

40. An infant formula comprising an oil obtained by a process according to claim 17.

41. A cosmetic composition comprising an oil obtained by a process according to claim 17.

42. A process for preparing a food product for humans or animals, said process comprising incorporating an oil obtained by a process according to claim 17 in said food product.

43. A process for preparing an infant formula, said process comprising incorporating an oil obtained by a process according to claim 17 in said infant formula.

44. A process for preparing a cosmetic composition, said process comprising incorporating an oil obtained by a process according to claim 17 in said composition.

45. The use of an oil obtained by a process according to claim 17 for the preparation of a food product for humans or animals.

46. The use of an oil obtained by a process according to claim 17 for the preparation of an infant formula.

47. The use of an oil obtained by a process according to claim 17 for the preparation of a cosmetic product.

48. A process for preparing a food product, in particular an infant formula, said process comprising (a) optionally, blending an oil (preferably containing ARA) according to claim or an oil obtained by a process according to claim with one or more other oils containing a PUFA (of which one oil preferably contains DHA); (b) mixing an oil (preferably containing ARA) according to claim or an oil obtained by a process according to claim or the blend obtained in (a) with an aqueous phase to obtain an emulsion (c) optionally, concentrating the emulsion; and (d) optionally, drying the emulsion to obtain a dried material.

49. A process for preparing a food product, in particular an infant formula, said process comprising mixing one or more oils, preferably one or more vegetable oils, or a blend of oils with an aqueous phase to obtain an emulsion; drying the emulsion to obtain a dried material; and adding an oil according to claim (preferably in encapsulated form) or an oil obtained by a process according to claim (preferably in encapsulated form) to the dried material.

50. A vegetable oil prepared by the process of claim 17, wherein the vegetable oil comprises a polyunsaturated fatty acid (LC-PUFA) having at least 20 carbon atoms which has (a) an anisidine value (AnV) of less than 25; (b) a peroxide value (POV) of less than 10; (c) a triglyceride content of greater than 90%; and/or (c) an Oil Stability Index (OSI) of greater than 5 hours at 80° C.

51. A process for obtaining a purified vegetable oil comprising an LC-PUFA, said process comprising purifying a crude oil as defined in claim 50.

52. A food product for humans or animals, comprising an oil according to claim 51.

53. An infant formula comprising an oil according to claim 51.

54. A cosmetic composition comprising an oil according to claim 51.

Description

EXAMPLES

[0117] Seeds containing 19% Arachidonic acid (with respect to total fatty acids) are obtained from transgenic Brassica plants that are transformed using the procedures described in WO2008009600.

[0118] The seeds have the following specifications (determined in accordance with the Official Grain Grading Guide, 2001 of the Canadian Grain Commission): distinctly green <2%, total damaged <5%.

[0119] The seeds, having a moisture content of 17 wt. %, are dried using a fluid bed drier. The bed temperature is 28° C. Conditioned air is used having a dew point of 10° C. The dried seeds have a moisture content of 8.5 wt. %.

[0120] Prior to further processing the dried seeds are stored at a temperature of minus 20° C.

[0121] After storage (3 months), the seeds are flaked using a conventional flaking process.

[0122] The flakes are subsequently heated to reach a temperature of 130° C. in 20 seconds using superheated steam. The flakes are maintained at this temperature for 1 minute, and cooled to 40° C. in 30 minutes.

[0123] Following the heat treatment, the flakes are fed to a cooled expeller to obtain a pressed oil. The biomass exiting the expeller is extracted using hexane (ratio hexane:biomass=5:1) in a submerged counter-current extractor at a temperature of 40° C. The hexane is evaporated, yielding a hexane-extracted oil. The pressed oil and hexane-extracted oil are combined resulting in a crude oil.

[0124] The crude oil is purified using degumming (acid treatment), alkali purifying (neutralization), and bleaching using standard techniques. After bleaching the oil is steam deodorized under vacuum at a temperature of 180° C.

[0125] The characteristics of the crude and refined oil are given in the table below.

TABLE-US-00001 EXAMPLE REFERENCE EXPERIMENT Crude oil Refined oil Crude oil Refined oil Anisidine 20 9 55 27 POV  5 <1  11 <1 Triglyceride 95% 97% 86% 88% content OSI at 80° C. >10 hrs >10 hrs 2 hrs 4 hrs

REFERENCE EXPERIMENT

[0126] Seeds as described in example 1 are treated as follows to recover the oil.

[0127] The seeds, having a moisture content of 17 wt. % are dried using a vertical open-flame grain dryer at a temperature of 70° C. resulting in a moisture content of 8.5 wt. %. Prior to further processing the dried seeds are stored at ambient temperature.

[0128] After storage (3 months), the seeds are flaked using a conventional flaking process.

[0129] After flaking the seeds are steamed at a temperature of 100° C. for 30 minutes.

[0130] Following the heat treatment, the flakes are fed to an expeller to obtain a pressed oil. The biomass exiting the expeller is extracted using hexane (ratio hexane:biomass=5:1) in a submerged counter-current extractor at a temperature of 40° C. The hexane is evaporated, yielding a hexane-extracted oil. The pressed oil and hexane-extracted oil are combined resulting in a crude oil.

[0131] The crude oil is purified using degumming (acid treatment), alkali purifying (neutralization), and bleaching using standard techniques. After bleaching the oil is steam deodorized under vacuum at a temperature of 180° C.

[0132] .sup.1H-NMR (to Determine Triglyceride Content)

[0133] About 12 mg of an oil sample is weighted accurately into a glass vial and about 12 mg p-nitrotoluene is weighted accurately on top. The sample is dissolved in CDCl.sub.3 and .sup.1H-NMR spectrum were recorded on a Bruker Avance III 600, equipped with a cryoprobe, operating at a proton frequency of 600 MHz and at a probe temperature of 300 K. The spectrum for quantification was recorded with a 60-90° excitation pulse using standard quantitative parameters with a relaxation delay of 30 s.