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TABLE 3.1.2
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Summary of analytical methods for ethyl carbamate (since 2000).
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LOD, g L 1 or g kg 1
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FTIR GC/MS CI-ITMS CI-MS/MS EI-MS/MS EI-MS/MS EI-SIM EI-SIM EI-SIM EI-SIM EI-SIM EI-SIM HPLC-FLD HPLC-FLD
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600 800
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1 0.6 10 30 a 0.1 <0.3b 0.5 3 9.6 4.2 20
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LC/MS/MS
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Value not given by authors. Estimated.
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ANALYSIS
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of mass selective detection, many laboratories still appear to have problems implementing the of cial method of analysis for wine (74, 75) or lengthy cleanup procedures are required to overcome interferences from matrix components (61). Jagerdeo et al. (58) demonstrated that multidimensional GC could be used to overcome the problem of matrix interferences and a limit of detection (LOD) of 1 g kg 1 could be attained in wines. Although a rapid extraction step using hyper-cross-linked hydroxylated polystyrenedivinylbenzene copolymer SPE (Isolute ENV+[Biotage]) columns could be used, subsequent analysis required specialist equipment comprising a GC with a ame ionization detector and a GC/MS system coupled using a cryogenic trap. More recently, Mirzoian and Mabud (70) combined the ENV+ SPE technique with GC/MS SIM and demonstrated satisfactory method performance for the analysis of selected alcoholic beverages. The ENV+ SPE columns are selective for small polar molecules and avoid the need for harmful chlorinated solvents. However, the recovery of ethyl carbamate is diminished by the presence of ethanol in samples and its removal, using for example, a vacuum centrifuge concentrator, can be time-consuming. Lachenmeier et al. (67) showed that MS/MS in combination with GC could be used to provide a rapid and reliable quanti cation of ethyl carbamate in stone-fruit spirits with minimal sample cleanup. In EI mode, characteristic transitions of m/z 74 44 and m/z 62 44 for ethyl carbamate, and m/z 64 44 for ethyl carbamate-d5 were followed using selected reaction monitoring (SRM). Using this technique, ethyl carbamate could be identi ed and quanti ed to an LOD of 10 g L 1. Hamlet et al. (59) used CI-MS/MS to measure low concentrations of ethyl carbamate in bread. Using positive ion CI with ammonia reagent gas to generate abundant [M+H]+ and [M+NH4]+ ions from ethyl carbamate, precursor to product transitions of m/z 107 90, m/z 107 62, and m/z 90 62 for ethyl carbamate and m/z 112 63 for the ethyl carbamate-d5 were monitored. This use of CI over EI resulted in a lower LOD for ethyl carbamate of 0.6 g kg 1. In the last 10 15 years, solid-phase microextraction (SPME), as discovered by Arthur and Pawliszyn (76), has emerged as a rapid, simple, solvent-free alternative to conventional extraction methods. SPME can dramatically reduce labor, materials, and solvent disposal costs, and is ideally suited to the analysis of aqueous samples such as alcoholic beverages (77). Whiton and Zoecklein (62) optimized an HS-SPME method for the analysis of ethyl carbamate in wine. Using propyl carbamate as internal standard and a carbowax/divinyl benzene SPME ber exposed to the sample headspace for 30 min, ethyl carbamate could be rapidly and reliably quanti ed to an LOD of about 10 g L 1. More recently, Lachenmeier et al. (68) used ethyl carbamate-d5 as internal standard and GC/MS/MS detection to develop an automated HS-SPME method for the con rmatory screening of ethyl carbamate in stone-fruit spirits. 3.1.3.2.2 HPLC Methods It is evident that reliable GC/MS analysis of ethyl carbamate requires either lengthy sample preparation procedures or
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ETHYL CARBAMATE (URETHANE)
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Figure 3.1.4 Formation of ethyl xanthen-9-ylcarbamate ( uorescent) from ethyl carbamate and 9-xanthydrol.
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expensive instrumentation such as MS/MS. However, other workers have demonstrated that HPLC-based methods could offer a simpler analytical alternative to the use of GC/MS, particularly for alcoholic beverages. Herbert et al. (53) developed a simple, rapid, and cost-effective method for the analysis of ethyl carbamate in wine brandy, forti ed wines, and table wines, using HPLCFLD. To achieve the required selectivity, a uorescent derivative of ethyl carbamate was prepared from the reagent 9-xanthydrol according to the scheme given in Fig. 3.1.4. Although 9-xanthydrol can form derivatives with, for example, amines and amino acids present naturally in alcoholic beverage such as wine, these did not interfere with the subsequent analysis. By using a simple dilution technique to normalize the ethanol content of samples to 20% prior to analysis, ethyl carbamate could be rapidly (40 min) and reliably measured to low concentrations (4.2 g L 1) with a method performance that was comparable to GC/MS. De Melo Abreu et al. (75) validated the HPLC-FLD method of Herbert et al. (53) by collaborative trial. Despite a limited number of participants (six), the results obtained by laboratories using the HPLC-FLD method (two) were comparable to those using GC/MS. Although HPLC-FLD may be suitable for the analysis of ethyl carbamate in alcoholic beverages, there might be limitations for other matrices. Park et al. (63) used propyl carbamate as internal standard and liquid liquid extraction (ethyl acetate) to isolate ethyl carbamate from soy sauce prior to derivatization with 9-xanthydrol. Both ethyl carbamate and propyl carbamate were well separated and free from interfering peaks in the chromatograms, but the LOD in soy sauce was about ve times higher (20 g L 1) than that obtained by Herbert et al. for alcoholic beverages. In the same publication, Park et al. (63) also described a method for the analysis of soy sauce using HPLC/MS/MS. Samples were prepared by SPE using dichloromethane for elution, and propyl carbamate as internal standard. After removal of the solvent, residues were dissolved in water, ltered, and injected directly into an HPLC/MS/MS system that was tted with an electrospray interface (ESI). The SRM precursor to product ion transitions was m/z 90 62 for ethyl carbamate and m/z 104 62 for propyl carbamate. The LOD for ethyl carbamate in soy sauce using this technique was 0.05 g L 1 for a sample-to- nal-extract ratio of 5 g mL 1. It is likely that with further development, for example, from the use
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