mintlactone and pulegone

A novel automated method was developed for the quantitative determination of nine terpenoids that could contribute to the minty notes of red wine bouquet. The method couples headspace SPME-Arrow extraction with GC-MS/MS analysis. PDMS/DVB fiber was chosen for the extraction and an ionization energy of 30 eV permitted to optimize the analyte detection. The optimal sample preparation consists of a two-fold dilution of the wine sample with addition of 4 g of sodium chloride while the most suitable extraction conditions take place at 50 °C for 1 h. The method shows good linearity, intraday variations between 2 and 25%, interday variations between 7 and 23% and recoveries between 80 and 119%. The method exhibits the required low detection (between 3 and 60 ng/L) and quantification (between 6 ng/L and 200 ng/L) limits. These limits have permitted the quantification of the pool of minty terpenoids in fourteen red Bordeaux wines.

Topics: Cyclohexane Monoterpenes; Dimethylpolysiloxanes; Eucalyptol; Gas Chromatography-Mass Spectrometry; Lactones; Limonene; Mentha; Menthol; Odorants; Polyvinyls; Solid Phase Microextraction; Tandem Mass Spectrometry; Terpenes; Wine

Starting from (R)-(+)- and (S)-(-)-pulegone, enantiomeric pairs of esters and lactones with the p-menthane system were obtained. The Claisen rearrangement of allylic alcohols and iodolactonization of gamma,delta-unsaturated acids were the key steps of syntheses presented. The structures of compounds were determined by both spectroscopic and crystallographic methods. Some of the synthesized compounds are characterized by interesting odoriferous properties.

Topics: Crystallography, X-Ray; Cyclohexane Monoterpenes; Lactones; Magnetic Resonance Spectroscopy; Mentha; Molecular Structure; Monoterpenes; Odorants; Oils, Volatile; Stereoisomerism; Terpenes