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Synthesis of Four Isomers of Parinaric Acid by Dmitry V. Kuklev; William L. Smith is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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A simple and reliable method for synthesizing four isomers of parinaric acid from ␣-linolenic acid (ALA) in high yields is described. The methylene-interrupted, cis triene system (1,4,7-octatriene) of ALA and common to other naturally occurring polyunsaturated fatty acids was transformed to a conjugated tetraene system (1,3,5,7-octatetraene). The synthesis involves bromination of ALA using 0.l M Br 2 in a saturated solution of NaBr in methanol, esterification of the fatty acid dibromides, double dehydrobromination by 1,8-diazabicyclo[5.4.0]undec-7-ene and saponification of the conjugated esters to a mixture of free conjugated acids. Addition of one molecule of bromine to the 12,13-double bond of ALA and subsequent dehydrobromination produces ␣-parinaric acid (9Z,11E,13E,15Z-octadecatetraenoic acid); addition of Br 2 to the 9,10-double bond or 15,16-double bond and then dehydrobromination and rearrangement yields 9E,11E,13E,15Z-octadecatetraenoic or 9E,11E,13E,15Z-octadecatetraenoic acids, respectively. The mixture of parinaric acid isomers is obtained in 65% yield, and the isomers can be purified by preparative HPLC; alternatively, the isomers can be converted by base catalyzed cis

Who reads Synthesis of Four Isomers of Parinaric Acid?

Author

Dmitry V. Kuklev; William L. Smith

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0009-3084)

Published

2004

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)