ABSTRACT
The degradation of the prostaglandin fenprostalene (III) was studied in aqueous solution. The reaction was both specific acid and base catalyzed. The only reaction found to occur was hydrolysis of the methyl ester at C-1. Activation energies for the acid- and base-catalyzed reactions were determined and are nearly identical to that for the hydrolysis of ethyl acetate, a model ester. A competing acid-catalyzed reaction of the C-1 free acid of III was found to be approximately 10 times slower than the hydrolysis of III.
Subject(s)
Prostaglandins F, Synthetic , Chromatography, High Pressure Liquid/methods , Drug Stability , Hydrogen-Ion Concentration , Kinetics , Prostaglandins F, Synthetic/analysis , Solutions , Time FactorsABSTRACT
A sensitive and specific analytical method was developed to determine the enantiomeric purity of naproxen. A simple derivatization of naproxen with (S)-(+)-2-octanol proceeded quantitatively and gave a mixture of diastereomeric esters displaying baseline separation on liquid chromatography. The ratio of these esters was the same as the ratio of enantiomers present in naproxen samples assayed. Reproducibility of the method was excellent.
Subject(s)
Naproxen/analysis , Chromatography, Liquid , Esterification , Methods , StereoisomerismSubject(s)
Prostaglandins , Drug Stability , Hydrogen-Ion Concentration , Kinetics , Mathematics , Methanol , Solvents , WaterSubject(s)
Anti-Inflammatory Agents/urine , Naphthaleneacetic Acids/urine , Animals , Biotransformation , Body Weight , Carbon Isotopes , Chromatography, Ion Exchange , Female , Glucuronates/urine , Guinea Pigs , Half-Life , Haplorhini , Humans , Hydrogen-Ion Concentration , Ion Exchange , Macaca , Male , Naphthaleneacetic Acids/metabolism , Rats , Species Specificity , Spectrophotometry, Ultraviolet , Swine , TritiumABSTRACT
The substance causing the peculiar odor in sweat of schizophrenic patients has been isolated and identified as trans-3-methyl-2-hexenoic acid by gas chromatography, mass spectrometry, and nuclear magnetic resonance spectroscopy. The natural and the synthetic compounds were cleaves across the double bond to give 2-pentanone and oxalic acid, thereby confirming the structure.
