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(12) United States Patent (10) Patent No.: US 8,946.460 B2 Petrie Et Al

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(12) United States Patent (10) Patent No.: US 8,946.460 B2 Petrie Et Al USOO894.646OB2 (12) United States Patent (10) Patent No.: US 8,946.460 B2 Petrie et al. (45) Date of Patent: Feb. 3, 2015 (54) PROCESS FOR PRODUCING (52) U.S. Cl. POLYUNSATURATED FATTY ACDS IN AN CPC. CIIB I/00 (2013.01); CIIC3/06 (2013.01); ESTERFED FORM CIIC3/003 (2013.01) USPC ............................ 554/124;554/224: 554/170 (71) Applicants: James Robertson Petrie, Goulburn (AU); Surinder Pal Singh, Downer (58) Field of Classification Search (AU); Robert Charles de Feyter, None Monash (AU) See application file for complete search history. (72) Inventors: James Robertson Petrie, Goulburn (56) References Cited (AU); Surinder Pal Singh, Downer U.S. PATENT DOCUMENTS (AU); Robert Charles de Feyter, Monash (AU) 4,399.216 A 8, 1983 Axel et al. 5,004,863. A 4, 1991 Umbeck 5,104,310 A 4, 1992 Saltin (73) Assignees: Commonwealth Scientific and 5,159,135 A 10, 1992 Umbeck et al. 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No.: 13/918,392 AU 776417 9, 2004 (Continued) (22) Filed: Jun. 14, 2013 OTHER PUBLICATIONS Prior Publication Data (65) Gul M.K., et al., Sterols and the phytosterol conent of oil seed rape US 2013/0338387 A1 Dec. 19, 2013 (Brassica napus L.), 2006, Journal of Cell and Molecular Biology, Related U.S. Application Data vol. 5, pp. 71-79.* (Continued) (60) Provisional application No. 61/782,680, filed on Mar. 14, 2013, provisional application No. 61/697,676, filed on Sep. 6, 2012, provisional application No. Primary Examiner – Yate K Cutliff 61/663,344, filed on Jun. 22, 2012, provisional (74) Attorney, Agent, or Firm — John P. White; Gary J. application No. 61/660,392, filed on Jun. 15, 2012. Gershik; Cooper & Dunham LLP (51) Int. C. (57) ABSTRACT C07C 67/00 (2006.01) The present invention relates to a process for producing ethyl A23D 9/00 (2006.01) esters of polyunsaturated fatty acids, comprising transesteri CIIB I/00 (2006.01) fying triacylglycerols in extracted plant lipid. CIIC3/06 (2006.01) CIIC3/00 (2006.01) 43 Claims, 21 Drawing Sheets aloyl-CoAacetyl-CoA ----------------------> 89 &2 ses. 8:23 2 A. S:36,9,12 GA S:SYS,2SA.A. '' 6 is as i GY 20:2.y.a. 23A8. , 4 A 8:43,3,2,355A; 26:383,34.7 \ sciss As els / 20:45,8,1,4 ARA 2:48, 4 EA \ 23 s y 20:5A58,3,4,7 EPA 8 Ss: assic 22:..., 0,389 (OA) ------ 24:5A9, $25,82 scies l is iss 22:6.4.7.0,3,6, 9 A -- 246A9,2,353.i -xcac, US 8,946.460 B2 Page 2 (56) References Cited 7,217,856 B2 5/2007 Weaver et al. 7,220,897 B2 5/2007 Mukerji et al. U.S. PATENT DOCUMENTS 7.241,619 B2 7/2007 Mukerji et al. 7,244,563 B2 7/2007 Cahoon et al. 5,463,174. A 10/1995 Moloney et al. 7,247.461 B2 7/2007 Metz et al. 5,504,200 A 4, 1996 Hall et al. 7,256,033 B2 8, 2007 Damude et al. 5,518,908 A 5, 1996 Corbinet al. 7,262,343 B1 8, 2007 DeBonte et al. 5,545,818 A 8, 1996 McBride et al. 7,271,315 B2 9/2007 Metz et al. 5,569,834. 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