Stereochemistry of alpha-parinaric acid fromImpatiens edgeworthii seed oil

M O Bagby; C R Smith Jr; I A Wolff

doi:10.1007/BF02531613

Stereochemistry of alpha-parinaric acid fromImpatiens edgeworthii seed oil

Lipids. 1966 Jul;1(4):263-7. doi: 10.1007/BF02531613.

Authors

M O Bagby¹, C R Smith Jr, I A Wolff

Affiliation

¹ Northern Regional Research Laboratory, Peoria, Illinois.

PMID: 17805627
DOI: 10.1007/BF02531613

Abstract

alpha-Parinaric acid is a major constituent fatty acid (48%) fromImpatiens edgeworthii Hook F. seed oil. Partial hydrazine reduction of the tetraene gave products which permit defining the stereochemistry of alpha-parinaric acid. Its structure iscis-9,trans-11,trans-13,cis-15-octadecatetraenoic acid. The tetraene readily reacts with maleic anhydride to give the Diels-Alder product with notrans-unsaturation. The formation of this adduct is contrary to previous reports.