Identification of omega hydroxy fatty acids in biological samples as their pentafluoropropyl derivatives by gas chromatography/mass spectrometry with positive and negative ion detection.
A simple one-step procedure for derivatization of the omega hydroxy fatty acids 20-hydroxyeicotetraeonic acid and 12-hydroxylauric acid is presented. The procedure involves acylation of the terminal hydroxy group and esterification of the carboxylic acid with a mixture of pentafluoropropionic anhydride and pentafluoropropanol. Positive and negative ion spectra for the derivatives are presented. The procedure was used to demonstrate conversion of arachidonic acid to 20-hydroxyeicosatetraeonic acid and lauric acid to 12-hydroxylauric acid in kidney microsomal incubations. The reaction appears to be specific, since derivatives of subterminal fatty acids (secondary alcohols) could not be detected.
University of Pittsburgh School of Pharmacy, Department of Pharmaceutical Sciences, 904 Salk Hall, Pittsburgh, PA 15261, USA. maz@pitt.edu
Michael
M
Zemaitis
Samuel
S
Poloyac
Reginald
R
Frye
D000818:Animals; D004952:Esters / Q000737:chemistry*; D005233:Fatty Alcohols / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D006893:Hydroxyeicosatetraenoic Acids / Q000032:analysis / Q000378:metabolism; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D007668:Kidney / Q000737:chemistry / Q000378:metabolism; D007850:Lauric Acids / Q000032:analysis; D008297:Male; D008861:Microsomes / Q000737:chemistry / Q000378:metabolism; D051381:Rats; D017207:Rats, Sprague-Dawley; D012996:Solutions
D004952:Esters; D005233:Fatty Alcohols; D006845:Hydrocarbons, Fluorinated; D006893:Hydroxyeicosatetraenoic Acids; D007202:Indicators and Reagents; D007850:Lauric Acids; D012996:Solutions; C055987:20-hydroxy-5,8,11,14-eicosatetraenoic acid