Determination of synthetic components in flavors by deuterium/hydrogen isotopic ratios

Stable oxygen isotope content of water of EU data-bank wines from Italy, France and Germany

“…Among the innovative methods for authenticity control and origin assignment of foods and beverages, stable isotope ratio analysis has gained remarkable importance within the last years for the quality assessment of wine, spirits, fruit juices, flavours, oils, honey and maple syrup [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. For the analysis of wine, the first officially adopted stable isotope method in the EU was the determination of the site-specific D/H ratio by NMR for wine ethanol, mainly to provide evidence of the addition of beet sugar [3].…”

The homo‐PADAM Protocol: Stereoselective and Operationally Simple Synthesis of α‐Oxo‐ or α‐Hydroxy‐γ‐acylaminoamides and Chromanes

“…This technique has been shown to be very useful in helping to geo‐locate drugs such as cocaine23, 24 and heroin24–28 and has been used to help link seizures of fully synthetic drugs such as methylamphetamine and MDMA. Stable isotope ratio analysis of benzaldehyde has shown that it is possible to discriminate between industrial sources of benzaldehyde and those that are botanically derived 7–9. Catalytic oxidation of toluene would be the most likely source of the benzaldehyde precursor for the so‐called 'nitrostyrene' route as this is the major industrial manufacturing method for benzaldehyde.…”

“…Other processes such as the benzal chloride route are not as predominant. Industrial benzaldehyde has been reported to be heavily deuterium‐enriched, with δ 2 H values as high as +720‰ 7–9. Therefore, a synthetic scheme commencing with an industrial source of benzaldehyde (δ 2 H = +552) and comprising only two steps, with few exchangeable hydrogen atoms, could be expected to result in a product with a positive δ 2 H value.…”

“…Although the purification processes such as recrystallization may affect the stable isotope ratios, a great deal of information may still be obtained from these measurements. Work conducted by the authors,5 and by Kurashima et al ,6 Butzenlechner et al 7 and Culp and Noakes,8, 9 has shown that industrial benzaldehyde produced by the catalytic oxidation of toluene has δ 2 H values that are positive, usually in the range +300 to +500‰ vs. VSMOW (Vienna Standard Mean Ocean Water). Previous work on the δ 13 C, δ 15 N and δ 2 H ratios in ephedrine and methylamphetamine performed by the authors5 and by Makino et al 10 demonstrated that ephedrine and pseudoephedrine that had been prepared by the semi‐synthetic process that employs this type of industrial benzaldehyde as a precursor also had positive δ 2 H values as did any methylamphetamine that was prepared from this source of ephedrine or pseudoephedrine 5, 6, 10, 11.…”

Gas chromatography ‐ isotope ratio mass spectrometry measurements of some carboxylic esters from different apple varieties

“…Gas chromatography-isotope ratio mass spectrometry (GC-IRMS) measurements are needed to detect such blends . Some GC-IRMS measurements of volatiles occurring in apples or apple containing food have been reported recently, for example Nitz et al (1992) reported on the analysis of components of a natural cis-3-hexen-1-01 fraction, Culp and Noakes (1992) determined the isotopic ratios of many natural and synthetic esters and Schmidt et al (1993) described the inter-and intramolecular isotope correlations of some other volatiles. However, comprehensive measurements of the 6'3Cp,,-values of the aroma components from apples are still unavailable.…”