Facile and stereoselective synthesis of (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid: Monounsaturated omega-3 fatty acids

Rawling, T; Duke, CC; Cui, PH; Murray, M

Facile and stereoselective synthesis of (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid: Monounsaturated omega-3 fatty acids

Rawling, T

Duke, CC Cui, PH Murray, M

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Publication Type:: Journal Article
Citation:: Lipids, 2010, 45 (2), pp. 159 - 165
Issue Date:: 2010-02-01

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Field	Value	Language
dc.contributor.author	Rawling, T https://orcid.org/0000-0002-6624-6586	en_US
dc.contributor.author	Duke, CC	en_US
dc.contributor.author	Cui, PH	en_US
dc.contributor.author	Murray, M	en_US
dc.date.available	2009-11-25	en_US
dc.date.issued	2010-02-01	en_US
dc.identifier.citation	Lipids, 2010, 45 (2), pp. 159 - 165	en_US
dc.identifier.issn	0024-4201	en_US
dc.identifier.uri	http://hdl.handle.net/10453/28485
dc.description.abstract	Facile syntheses of the monounsaturated omega-3 fatty acids, (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid, are presented. Commercially available hydroxy fatty acids were esterified and oxidised, followed by the Wittig reaction to introduce the omega-3 olefinic bond; hydrolysis yielded the omega-3 fatty acids in high purity. An examination of different reaction conditions for the Wittig step found that THF as solvent and coupling temperatures of -78 °C gave optimal stereoselectivity, affording the omega-3 olefins in Z:E ratios 97:3. The syntheses have overall yields of ~43%, and utilise straightforward, robust chemistry, that may be readily scaled up and reproduced. Also presented is a method for accurately determining the double bond geometry and isomeric purity of the fatty acid products using 1H-13C-HSQC NMR and GC-MS, respectively. © 2010 AOCS.	en_US
dc.relation.ispartof	Lipids	en_US
dc.relation.isbasedon	10.1007/s11745-009-3378-3	en_US
dc.subject.classification	Nutrition & Dietetics	en_US
dc.subject.mesh	Fatty Acids, Omega-3	en_US
dc.subject.mesh	Fatty Acids, Monounsaturated	en_US
dc.subject.mesh	Oleic Acids	en_US
dc.subject.mesh	Nuclear Magnetic Resonance, Biomolecular	en_US
dc.subject.mesh	Stereoisomerism	en_US
dc.title	Facile and stereoselective synthesis of (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid: Monounsaturated omega-3 fatty acids	en_US
dc.type	Journal Article
utslib.citation.volume	2	en_US
utslib.citation.volume	45	en_US
utslib.for	1115 Pharmacology and Pharmaceutical Sciences	en_US
utslib.for	07 Agricultural and Veterinary Sciences	en_US
utslib.for	09 Engineering	en_US
utslib.for	11 Medical and Health Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
utslib.copyright.status	closed_access
pubs.issue	2	en_US
pubs.publication-status	Published	en_US
pubs.volume	45	en_US

Abstract:

Facile syntheses of the monounsaturated omega-3 fatty acids, (Z)-15-octadecenoic acid and (Z)-16-nonadecenoic acid, are presented. Commercially available hydroxy fatty acids were esterified and oxidised, followed by the Wittig reaction to introduce the omega-3 olefinic bond; hydrolysis yielded the omega-3 fatty acids in high purity. An examination of different reaction conditions for the Wittig step found that THF as solvent and coupling temperatures of -78 °C gave optimal stereoselectivity, affording the omega-3 olefins in Z:E ratios 97:3. The syntheses have overall yields of ~43%, and utilise straightforward, robust chemistry, that may be readily scaled up and reproduced. Also presented is a method for accurately determining the double bond geometry and isomeric purity of the fatty acid products using 1H-13C-HSQC NMR and GC-MS, respectively. © 2010 AOCS.

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http://hdl.handle.net/10453/28485