Antioxidant triacylglycerols and lipid compositions
View Patent ↗A lipid composition includes triacylglycerols that include unsaturated fatty acids such as alpha linolenic acid and antioxidant moeities such as pyruvic acid.
1. A nutraceutical comprising a mixture of triacylglycerols which comprises:
(a) greater than about 10 mol % unsaturated long chain fatty acid esters comprising C18 fatty acids including omega-3, omega-6 and omega-9 fatty acids, wherein the ratio of omega-3 fatty acids to omega-6 fatty acids is greater than about 2, and
(b) greater than about 10 mol % antioxidant non-fatty carboxylic acid esterified to a triacylglycerol.
2. The nutraceutical of claim 1 wherein the ratio of omega-3 fatty acids to omega-6 fatty acids is greater than about 3.
3. The nutraceutical of claim 1 wherein the omega-3 fatty acids comprise α-linolenic acid, the omega-6 fatty acids comprise linoleic acid and the omega-9 fatty acids comprise oleic acid.
4. The nutraceutical of claim 3 wherein the concentration of α-linolenic acid is greater than about 30 mol %.
5. The nutraceutical of claim 1 wherein the concentration of the antioxidant ester is greater than about 25% on a molar basis.
6. The nutraceutical of claim 1 wherein the concentration of the antioxidant ester is greater than about 30% on a molar basis.
7. The nutraceutical of claim 1 wherein the antioxidant ester comprises pyruvic acid or α-ketoglutaric acid.
8. The nutraceutical of claim 1 further comprising a saturated fatty acid ester and wherein a ratio of unsaturated long chain fatty acid ester to saturated fatty acid ester is greater than about 3.5.
9. The nutraceutical of claim 8 wherein the ratio of unsaturated long chain fatty acid ester to saturated fatty acid ester is greater than about 7.
10. A method of preparing the nutraceutical of claim 1 comprising the step of interesterifying a source oil or triacylglycerol mixture with an antioxidant non-fatty carboxylic acid, using a lipase catalyst.
11. The method of claim 10 wherein the lipase catalyst is sn-1 or sn-3, or sn-1 and sn-3, regiospecific.
12. The method of claim 10 wherein the source oil is selected from the group consisting of perilla oil and flaxseed oil.
13. The method of claim 10 wherein the antioxidant non-fatty carboxylic acid is an alpha-keto acid.
14. The method of claim 13 wherein the alpha-keto acid is pyruvic acid or ester thereof.
15. A nutraceutical comprising a mixture of triacylglycerols comprising
(a) unsaturated long chain fatty acid esters comprising unsaturated C18 fatty acids including omega-3, omega-6 and omega-9 fatty acids, wherein the ratio of omega-3 fatty acids to omega-6 fatty acids is greater than about 2, and
(b) antioxidant non-fatty acid carboxylic acid esters, wherein the mixture has a peroxide value of about 6.5 meq/kg or less.
16. The nutraceutical of claim 15 wherein the ratio of omega-3 fatty acids to omega-6 fatty acids is greater than about 3.
17. The nutraceutical of claim 15 wherein the omega-3 fatty acids comprise α-linolenic acid, the omega-6 fatty acids comprise linoleic acid and the omega-9 fatty acids comprise oleic acid.
18. The nutraceutical of claim 17 wherein the concentration of α-linolenic acid is greater than about 30 mol %.
19. The nutraceutical of claim 15 wherein the concentration of the antioxidant ester is greater than about 25% on a molar basis.
20. The nutraceutical of claim 19 wherein the concentration of the antioxidant ester is greater than about 30% on a molar basis.
21. The nutraceutical of claim 15 wherein the antioxidant ester comprises pyruvic acid or α-ketoglutaric acid.
22. The nutraceutical of claim 15 further comprising a saturated fatty acid ester and wherein a ratio of unsaturated long chain fatty acid ester to saturated fatty acid ester is greater than about 3.5.
23. The nutraceutical of claim 22 wherein the ratio of unsaturated long chain fatty acid ester to saturated fatty acid ester is greater than about 7.