Ethyl carbamate: analytical methodology, occurrence, formation, biological activity and risk assessment

Mutation Research/Genetic Toxicology - Tập 259 - Trang 325-350 - 1991
B. Zimmerli1, J. Schlatter1
1Swiss Federal Office of Public Health, Division of Food Science, Berne Switzerland

Tài liệu tham khảo

Adam, 1987, Gaschromatographische Bestimmung von Ethylcarbamat (Urethan) in Spirituosen, Branntweinwirtschaft, 127, 66 Adam, 1990, Bestimmung von Ethylcarbamat in extrakthaltigen und extraktfreien Spirituosen, Branntweinwirtschaft, 130, 170 Adams, 1965, Esters of carbamic acid, Chem. Rev., 65, 567, 10.1021/cr60237a002 Allen, 1964, Decomposition of carbamylphosphate in aqueous solution, Biochemistry, 3, 1231, 10.1021/bi00897a010 Almy, 1989, Urea analysis for wines, J. Agric. Food Chem., 37, 968, 10.1021/jf00088a031 Altmann, 1990 Andrey, D. (1986 and 1987) personal communications. Andrey, 1987, A simple gas chromatography method for the determination of ethylcarbamate in spirits, Z. Lebensm. Unters. Forsch., 185, 21, 10.1007/BF01083335 1967, Toxicological evaluation of some antimicrobials, antioxidants, emulsifiers, stabilizers, flour-treatment agents, acids and bases, 104 1972, WHO Food Add. Ser., 4, 67 1985 1986 1988, Dimethyl dicarbonate cleared for wine under constituents policy, 30 1988, Konservierungsmittel in Brot, 19 1989, Mitt. Gebiete Lebensm. Hyg., 80, 277 1990, Ethylcarbamate formation in beer linked to bottle cap agent, 44 Aylott, 1987, Determination of ethyl carbamate in distilled spirits using nitrogen specific and mass spectrometric detection, J. Inst. Brew., 93, 382, 10.1002/j.2050-0416.1987.tb04521.x Aylott, 1990, Ethyl carbamate formation in grain based spirits, 96, 213 Bailey, 1986, Determination of ethyl carbamate in alcoholic beverages by methylation and gas chromatography with nitrogen-phosphorus thermionic detection, J. Chromatogr., 369, 199, 10.1016/S0021-9673(00)90116-X Bateman, 1976, The mutagenic action of urethane, Mutation Res., 39, 75, 10.1016/0165-1110(76)90013-0 Battaglia, 1988, Die Bildung von Ethylcarbamat bei der Vergärung von Zwetschgenmaischen, Mitt. Gebiete Lebensm. Hyg., 79, 343 Battaglia, 1990, Ethyl carbamate (urethane) in alcoholic beverages and foods: a review, Food Add. Contam., 7, 477, 10.1080/02652039009373910 Baumann, 1986, Gaschromatographische Bestimmung von Urethan (Ethylcarbamat) in alkoholischen Getränken, Mitt. Gebiete Lebensm. Hyg., 77, 327 Baumann, 1986, Entstehung von Urethan (Ethylcarbamat) in alkoholischen Getränken, Schweiz. Z. Obst- Weinbau, 122, 602 Baumann, 1987, Zur Bildungsweise von Ethylcarbamat (Urethan) in Steinobstdestillaten, Mitt. Gebiete Lebensm. Hyg., 78, 317 Baumann, 1988, Beschleunigte Ethylcarbamatbildung in Spirituosen, Mitt. Gebiete Lebensm. Hyg., 79, 175 Bebiolka, 1987, Bestimmung von Ethylcarbamat in alkoholischen Getränken mittels Kapillargaschromatographie/Massenspektrometrie, Dtsch. Lebensm. Rdsch., 83, 75 Bertrand, 1988, Dosage du carbamate d'éthyle dans les vins et les eaux-de-vie, Conn. Vigne Vin, 22, 39 Bertrand, 1986, Le carbamate d'éthyl dans les eaux-de-vie de vin, 20, 131 Bertrand, 1990, Elimination du précurseur du carbamate d'éthyle dans les eaux-de-vie de vin, Conn. Vigne Vin, 23, 195 Boughton, 1966, Dissociation constants of hydropseudohalic acids, J. Inorg. Nucl. Chem., 28, 2851, 10.1016/0022-1902(66)80011-8 Brodbelt, 1987, Chemical ionization in an ion trap mass spectrometer, Anal. Chem., 59, 1278, 10.1021/ac00136a007 Brotherton, 1959, The synthesis and chemistry of cyanogen, Chem. Rev., 59, 841, 10.1021/cr50029a003 Brumley, 1988, Quantitation of ethyl carbamate in whiskey, sherry, port, and wine by gaschromatography/tandem mass spectrometry using a triple quadrupole mass spectrometer, Anal. Chem., 60, 975, 10.1021/ac00161a006 Brümmer, 1984, Massnahmen zur Schimmelbekämpfung bei Brot, Getreide Mehl Brot, 38, 52 Cairns, 1987, Residue levels of ethyl carbamate in wines and spirits by gas chromatography and mass spectrometry/mass spectrometry, Anal. Chem., 59, 2055, 10.1021/ac00144a010 Canas, 1988, Rapid gas chromatography method for determining ethyl carbamate in alcoholic beverages with thermal energy analyzer detection, J. Ass. Offic. Anal. Chem., 71, 509 Canas, 1989, Ethyl carbamate levels in selected foods and beverages, J. Ass. Offic. Anal. Chem., 72, 873 Cejka, 1968, Carbamylation of globin in electrophoresis and chromatography in the presence of urea, Biochim. Biophys. Acta, 154, 589, 10.1016/0005-2795(68)90021-4 Christmann, 1988, Urethangehalte in deutschen Weinen, Weinwirtschaft-Technik, 124, 6 Christoph, 1989, Verfahren zum Reinigen von Obstbranntweinen und Spirituosen, Food Sci. Technol. Abstracts, 21, 215 Christoph, 1986, Untersuchungen zur Bildung und zum Destillationsverhalten von Aethylcarbamat bei der Branntweinherstellung, Alkohol-Industrie, 99, 347 Christoph, 1987, Ethylcarbamat in Obstbranntweinen, 41, 67 Christoph, 1987, Ethylcarbamat in Obstbranntweinen, Alkohol-Industrie, 100, 369 Christoph, 1987, Ethylcarbamat in Obstbranntweinen, Alkohol-Industrie, 100, 404 Christoph, 1988, Ethylcarbamat in Obstbranntweinen, Alkohol-Industrie, 101, 342 Christoph, 1988, Ethylcarbamat in Obstbranntweinen, Alkohol-Industrie, 101, 369 Cicerone, 1983, The atmospheric chemistry of hydrogen cyanide (HCN), J. Geophys. Res., 88, 10689, 10.1029/JC088iC15p10689 Clegg, 1988, Detection and quantitation of trace levels of ethyl carbamate in alcoholic beverages by selected ion monitoring, J. Agric. Food Chem., 36, 502, 10.1021/jf00081a024 Clegg, 1988, Contamination of alcoholic products by trace quantities of ethyl carbamate (urethane), Bull. Environ. Contam. Toxicol., 41, 832, 10.1007/BF02021042 Conacher, 1986, Ethyl carbamate in alcoholic beverages: a Canadian case history, 237 Conacher, 1987, Capillary column gas chromatographic determination of ethyl carbamate in alcoholic beverages with confirmation by gas chromatography/mass spectrometry, J. Ass. Offic. Anal. Chem., 70, 749 Cook, 1990, Ethyl carbamate formation in grain-based spirits, 96, 233 Dahl, 1980, Comparative carcinogenicities and mutagenicities of vinyl carbamate, ethyl carbamate and ethyl N-hydroxycarbamate, Cancer Res., 40, 1194 Dennis, 1986, Method for the analysis of ethyl carbamate in alcoholic beverages by capillary gas chromatography, J. Chromatogr., 369, 193, 10.1016/S0021-9673(00)90115-8 Dennis, 1988, Ethyl carbamate analysis in fermented products: a comparison of measurements of mass spectrometry, thermal energy analyzer, and Hall electrolytic conductivity detector, J. Res. Nat. Bureau Standards, 93, 249, 10.6028/jres.093.033 Dennis, 1989, Investigation of ethyl carbamate levels in some fermented foods and alcoholic beverages, Food Add. Contam., 6, 383, 10.1080/02652038909373794 Dennis, 1990, Cooperative trial studies on the analysis of ethyl carbamate using capillary gas chromatography, J. High Resol. Chromatogr., 13, 247, 10.1002/jhrc.1240130407 de Serres, 1981 Drexler, 1989, A gas chromatographic method for the determination of ethyl carbamate in spirits, Ernährung/Nutrition, 13, 591 Eichelberger, 1987, Existence of self chemical ionization in the ion trap detector, Anal. Chem., 59, 2730, 10.1021/ac00149a021 Erb, 1981, Der Blausäuregehalt von Getreidearten gemässigter Klimazonen, Z. Lebensm. Unters. Forsch., 173, 176, 10.1007/BF01041977 Ewart, 1988, Changes in flour thiols during storage, and improver action, Food Chem., 30, 231, 10.1016/0308-8146(88)90125-2 Field, 1988, Hazards of urethane (ethyl carbamate): a review of the literature, Lab. Anim., 22, 255, 10.1258/002367788780746331 Fossa, 1985, Distribution of urethane and its binding to DNA, RNA and protein in SENCAR and BALB/c mice following oral and dermal administration, J. Toxicol. Environ. Health, 15, 635, 10.1080/15287398509530692 Friederich, 1970, Introduction of the cyano group into the molecule, 67 Fröhlich, 1989, Genotoxizitätsprüfung mit Drosophila melanogaster: Neue Testerstämme mit erhöhter metabolischer Kapazität Fröhlich, 1988, Validation of an efficient in vivo genotoxicity test with somatic cells of Drosophila, Mutation Res., 203, 211, 10.1016/0165-1161(88)90126-4 Frost, 1964, Kinetik und Mechanismen homogener chemischer Reaktionen, 287 Funch, 1988, Analysis of ethyl carbamate in alcoholic beverages, Z. Lebensm. Unters. Forsch., 186, 29, 10.1007/BF01027176 Gaetano, 1987, Dosage du carbamate d'éthyle dans les vins et spiritueux par chromatographie en phase gazeuse/spectrométrie de masse, Bull. OIV, 60, 36 Gupta, 1989, In vitro formation of organ-specific ultimate carcinogens of 4-dimethylaminoazobenzene and urethane by microsomes, Toxicol. Lett., 45, 49, 10.1016/0378-4274(89)90158-6 Hagel, 1971, Cyanate formation in solutions of urea, 243, 366 Halmann, 1962, Kinetic and tracer studies of the reactions of carbamyl phosphate in aqueous solution, J. Chem. Soc., 1944, 10.1039/jr9620001944 Hara, 1988, Formation of ethylcarbamate in the model alcoholic beverages containing urea or its related compounds, J. Brew. Soc. Japan, 83, 57, 10.6013/jbrewsocjapan1988.83.57 Hartman, 1989, Determination of ethyl carbamate in commercial protein based condiment sauces by gas chromatography-mass spectrometry, J. Food Safety, 9, 173, 10.1111/j.1745-4565.1988.tb00518.x Henschke, 1989, Summary of Professor Ough's work at the Institute, 62, 2 Hurst, 1990, Measurement of ethyl carbamate in blood by capillary gas chromatography/mass spectrometry using selected ion monitoring, Biomed. Environ. Mass Spectr., 19, 27, 10.1002/bms.1200190104 IARC, 1974, Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man: Some Antithyroid and Related Substances, Vol. 7, 111 IARC, 1988, Monographs on the Evaluation of the Carcinogenic Risk to Humans, Vol. 44, 105 Ingledew, 1987, Yeast foods and ethyl carbamate formation in wine, Am. J. Enol. Viticol., 38, 332 Ito, 1988, Direct conversion of benzene to hydroquinone, 53, 296 Jardim, 1986, The role of cupric ions in the generation of superoxide in natural waters, Sci. Total Environ., 58, 47, 10.1016/0048-9697(86)90074-4 Jensen, 1958, On the kinetics of the decomposition of cyanic acid, Acta Chem. Scand., 12, 1657, 10.3891/acta.chem.scand.12-1657 Jensen, 1966, Alkyl cyanates, 20, 2091 Joe, 1977, Determination of urethane in wines by gas-liquid chromatography and its confirmation by mass spectrometry, J. Ass. Offic. Anal. Chem., 60, 509 Jones, 1960, Chemical and enzymatic synthesis of carbamyl phosphate, 46, 1194 Kada, 1980, Environmental Mutagens Data Book No. 1, 411 Kobashi, 1988, Removal of urea from alcoholic beverages with acid urease, J. Appl. Toxicol., 8, 73, 10.1002/jat.2550080112 Kobayashi, 1987, Determination of ethyl carbamate in sake by alkylation and gas chromatography with a flame ionization detector, J. Food. Hyg. Soc. Japan, 28, 330, 10.3358/shokueishi.28.330 Kobayashi, 1987, Determination of ethyl carbamate in sake by alkylation and gas chromatography with a flame ionization detector, J. Food. Hyg. Soc. Japan, 28, 492, 10.3358/shokueishi.28.492 Kristiansen, 1990, Chronic ethanol intake and reduction of lung tumors from urethane in strain A mice, Food Chem. Toxiol., 28, 35, 10.1016/0278-6915(90)90133-8 Laib, 1981, DNA alkylation by vinyl chloride metabolites: etheno derivatives or 7-alkylation of guanine?, Chem.-Biol. Interact., 37, 219, 10.1016/0009-2797(81)90179-4 Lau, 1987, Gas chromatographic-mass spectrometric determination of ethyl carbamate in alcoholic beverages, J. Chromatogr., 402, 233, 10.1016/0021-9673(87)80021-3 Lehmann, 1979, Über die Reaktion zwischen Kohlenhydraten und Aminosäuren, Z. Lebensm. Unters. Forsch., 169, 357, 10.1007/BF01127008 Lehmann, 1981, Über das Vorkommen und die Entstehung von Blausäure in Lebensmitteln, Lebensm. Gerichtl. Chem., 35, 55 Lehmann, 1979, Über den Blausäuregehalt von Getreide und Getreideprodukten, Z. Ernährungswiss, 18, 16, 10.1007/BF02026532 Leithauser, 1990, 1,N6-ethenoadenosine formation, mutagenicity and murine tumor induction as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethane) and vinyl carbamate, Carcinogenesis, 11, 463, 10.1093/carcin/11.3.463 Lieber, 1987, Metabolism and metabolic effects of ethanol, including interaction with drugs, carcinogens and nutrition, Mutation Res., 186, 201, 10.1016/0165-1110(87)90004-2 Lieber, 1987, The microsomal ethanol oxidizing system and its interaction with other drugs, carcinogens, and vitamins, 492, 11 Loev, 1963, An improved synthesis of carbamates, J. Org. Chem., 28, 3421, 10.1021/jo01047a033 Lutz, 1979, In vivo covalent binding of organic chemicals to DNA as a quantitative indicator in the process of chemical carcinogenesis, Mutation Res., 65, 289, 10.1016/0165-1110(79)90006-X MacKenzie, 1990, Ethyl carbamate formation in grain based spirits, 96, 223 MacNamara, 1989, Direct quantification of ethyl carbamate in distilled alcoholic beverages using a cold capillary injection system and optimised selected ion monitoring, Chromatographia, 27, 209, 10.1007/BF02260448 Maier, 1988, Carboxime (isofulmic acid), Angew. Chem. Int. Ed. Engl., 27, 938, 10.1002/anie.198809381 Martell, 1982, Chelates of ascorbic acid. Formation and catalytic properties, 153 McGill, 1990, Ethyl carbamate formation in grain spirits, 96, 245 McLucky, 1988, Self chemical ionization in an ion trap mass spectrometer, Anal. Chem., 60, 2312, 10.1021/ac00171a033 Mildau, 1987, Ethylcarbamat (Urethan) in alkoholischen Getränken: Verbesserte Analyse und lichtabhängige Bildung, Dtsch. Lebensm. Rdsch., 83, 69 Miller, 1983, The metabolic activation and nucleic acid adducts of naturally-occurring carcinogens: recent results with ethyl carbamate and the spice flavors safrole and estragole, Br. J. Cancer, 48, 1, 10.1038/bjc.1983.151 Mirvish, 1968, The carcinogenic action and metabolism of urethane and N-hydroxyurethane, Adv. Cancer Res., 11, 1, 10.1016/S0065-230X(08)60386-3 Möller, 1984, Über das Vorkommen und die Entstehung von Blausäure in Nahrungsmitteln Monteiro, 1989, Ethyl carbamate formation in wine: use of radioactively labeled precursors to demonstrate the involvement of urea, Am. J. Enol. Vitic., 40, 1 Mossoba, 1988, Application of gas chromatography/matrix isolation/Fourier transform infrared spectrometry to the determination of ethyl carbamate in alcoholic beverages and foods, Anal. Chem., 60, 945, 10.1021/ac00160a022 National Cancer Institute, 1978, Survey of Compounds which have been Tested for Carcinogenic Activity NIOSH, 1985 Nofre, 1989, Heterocyclic derivatives of N-carbamoyl, N-thiocarbamoyl- or N-amidino-aminomalonyl or aminosuccinyl amides and their use as sweeteners, Food Sci. Technol. Abstracts, 21, 223 Nofre, 1989, Heterocyclic derivatives of N-carbamoyl-, N-thiocarbamoyl- or N-amidino-glycine or β-alanine and their use as sweeteners, Food Sci. Technol. Abstr., 21, 223 Nomeir, 1989, Comparative metabolism and disposition of ethyl carbamate (urethane) in male Fischer 344 rats and male B6C3F1 mice, Toxicol. Appl. Pharmacol., 97, 203, 10.1016/0041-008X(89)90326-8 Nomura, 1976, Comparison of tumor susceptibility among various organs of foetal, young and adult ICR/Jcl mice, Br. J. Cancer, 33, 521, 10.1038/bjc.1976.83 O'Flaherty, 1983, The kinetics of urethane elimination in the mouse, Toxicol. Appl. Pharmacol., 68, 354, 10.1016/0041-008X(83)90278-8 Ough, 1976, Ethylcarbamate in fermented beverages and foods, 24, 323 Ough, 1976, Ethylcarbamate in fermented beverages and foods, 24, 328 Ough, 1978, A Davis scientist reviews an excellent fungicide, DEDC, Wines Vines, 59, 30 Ough, 1988, Urea removal from wines by an acid urease, Am. J. Enol. Vitic., 39, 303 Ough, 1988, Carbamyl compound reactions with ethanol, Am. J. Enol. Vitic., 39, 239 Ough, 1988, Formation of ethyl carbamate precursors during grape juice (chardonnay) fermentation, 39, 243 Ough, 1989, Preliminary comments of effects of grape vineyard nitrogen fertilization on the subsequent ethyl carbamate formation in wines, Am. J. Enol. Vitic., 40, 219 Ough, 1990, Factors contributing to urea formation in commercially fermented wines, Am. J. Enol. Vitic., 41, 68 Pafumi, 1987, Cake shelf life extension, Food Technol. Aust., 39, 286 Pierce, 1988, Determination of ethyl carbamate in distilled alcoholic beverages by gas chromatography with flame ionization or mass spectrometric detection, J. Ass. Offic. Anal. Chem., 71, 781 Port, 1976, Some examples of dose-response studies in chemical carcinogenesis, Oncology, 33, 66, 10.1159/000225107 Ratnayake, 1988, Preparation of Omega-3 PUFA concentrates from fish oil via urea complexation, Fat. Sci. Technol., 90, 381 Ribovich, 1982, Labeled 1,N6-ethenoadenosine and 3,N4-ethenocytidine in hepatic RNA of mice given [ethyl-1,2-3H or ethyl-1-14C]ethyl carbamate (urethan), Carcinogenesis, 3, 539, 10.1093/carcin/3.5.539 Riffkin, 1989, The possible involvement of Cu2+ peptide/protein complexes in the formation of ethyl carbamate, J. Inst. Brew., 95, 121, 10.1002/j.2050-0416.1989.tb04619.x Riffkin, 1989, Ethyl carbamate formation in the production of pot still whisky, J. Inst. Brew., 95, 115, 10.1002/j.2050-0416.1989.tb04618.x Ritzmann, 1987, Herstellung von Steinobstdestillaten mittels einer Raschigringkolonne, Früchte Gemüse, 54, 530 Ritzmann, 1988, Herstellung von ethylcarbamat-armen Steinobstdestillaten mittels RaschigringKolonne, Schweiz. Z. Obst- Weinbau, 124, 294 Scarpa, 1983, Superoxide ion as active intermediate in the auto-oxidation of ascorbate by molecular oxygen, 258, 6695 Scherer, 1986, Modification of DNA and metabolism of ethyl carbamate in vivo: formation of 7-(2-oxoethyl) guanine and its sensitive determination by reductive tritiation using 3H-sodium borohydride, IARC Sci. Publ., 70, 109 Schlatter, 1990, The carcinogenic potential of ethyl carbamate (urethane): risk assessment at human dietary exposure levels, Food Chem. Toxicol., 28, 205, 10.1016/0278-6915(90)90008-B Schlesinger, 1973, Equilibrium and kinetics of glyconitrile formation in aqueous solutions, J. Am. Chem. Soc., 95, 3729, 10.1021/ja00792a043 Schmähl, 1977, A dose-response study on urethane carcinogenesis in rats and mice, Int. J. Cancer, 19, 77, 10.1002/ijc.2910190111 Schmeltz, 1978, Formation and determination of ethyl carbamate in tobacco and tobacco smoke, J. Anal. Toxicol., 2, 265, 10.1093/jat/2.6.265 Schmidt, 1988, Beitrag zur Herstellung von urethanarmen Steinobstdestillaten, Branntweinwirtschaft, 128, 122 Schulz, 1986, Ethylcarbamat (Urethan) in Steinobstbranntweinen, 12/86, 1215 Schwarzer, 1975, Die Behandlung von cyanidhaltigem Galvanik-Abwasser mit Wasserstoffperoxid, Galvanotechnik, 66, 22 Shephard, 1987, Assessment of the risk of formation of carcinogenic N-nitroso compounds from dietary precursors in the stomach, Food Chem. Toxicol., 25, 91, 10.1016/0278-6915(87)90311-5 Smyth, 1967, Carbamylation of amino and tyrosin hydroxyl groups, J. Biol. Chem., 141, 1579, 10.1016/S0021-9258(18)96131-4 Solymosy, 1978, On the amounts of urethane formed in diethyl pyrocarbonate treated beverages, J. Agric. Food Chem., 26, 500, 10.1021/jf60216a025 Stark, 1964, On the reversible reaction of cyanate with sulfhydryl groups and the determination of NH2-terminal cysteine and cystine in proteins, J. Biol. Chem., 239, 1411, 10.1016/S0021-9258(18)91330-X Stark, 1965, Reactions of cyanate with functional groups of proteins, 4, 1030 Stark, 1965, Reactions of cyanate with functional groups of proteins, 4, 2363 Stark, 1960, Reaction of the cyanate present in aqueous urea with amino acids and proteins, J. Biol. Chem., 235, 3177, 10.1016/S0021-9258(20)81332-5 Stevens, 1962, The photo-oxidation of biacetyl solutions, J. Chem. Soc., 2813, 10.1039/jr9620002813 Suizu, 1990, Construction of urea non-producing yeast Saccharomyces cerevisiae by disruption of the CAR1 gene, Agric. Biol. Chem., 54, 537, 10.1271/bbb1961.54.537 Svensson, 1988, Alkylation of protein and DNA in mice treated with urethane, Carcinogenesis, 9, 2197, 10.1093/carcin/9.12.2197 Tadera, 1988, Participation of hydroxyl radical in hydroxylation of pyridoxine by ascorbic acid, Agric. Biol. Chem., 52, 2359, 10.1271/bbb1961.52.2359 Tanner, H. (1985) Personal communication. Tanner, 1986, Experiments to avoid high urethane-concentrations in distilled spirits, 255 Tanner, 1986, Möglichkeiten zur Reduktion des Urethangehaltes in Steinobstdestillaten, Schweiz. Z. Obst-Weinbau, 122, 260 Tanner, H. (1986c) Personal communication. Tanner, 1987, Zur Herstellung urethanarmer Steinobstdestillaten, Schweiz. Z. Obst- Weinbau, 123, 661 Tegmo-Larsson, I.-M. (1989) personal communication. Tegmo-Larsson, 1990, The effect of fermentation and extended lees contact on ethyl carbamate formation in New York wine, Am. J. Enol. Vitic., 41 Tegmo-Larsson, 1990, Ethyl carbamate precursors in grape juice and the efficiency of acid urease on their removal, Am. J. Enol. Vitic., 41 Tegmo-Larsson, 1990, Temperature and light effects on ethyl carbamate formation in wine during storage, J. Food Sci., 55, 10.1111/j.1365-2621.1990.tb01624.x Tegmo-Larsson, 1989, Effect of malolactic fermentation on ethyl carbamate formation in Chardonnay wine, Am. J. Enol. Vitic., 40, 106 Totsuka, 1988, Variation of urea and ammonium contents during wine making, J. Brew. Soc. Japan, 83, 424, 10.6013/jbrewsocjapan1988.83.424 Tourlière, 1989 Tuor, A. (1986) Personal communication. Turro, 1978 Van Ingen, 1987, Determination of ethyl carbamate in alcoholic beverages of two-dimensional gas chromatography, J. High Resol. Chrom. Commun., 10, 151, 10.1002/jhrc.1240100310 Vogels, 1969, Hydrolysis of allantoate, Recl. Trav. Chim. Pays-Bas, 88, 951, 10.1002/recl.19690880808 Vogels, 1970, Cyanate decomposition catalyzed by certain bivalent anions, Recl. Trav. Chim. Pays-Bas, 89, 500, 10.1002/recl.19700890507 Vogt, 1948, Mutationsauslösung bei Drosophila durch Aethylurethan, Experientia, IV/2, 68, 10.1007/BF02155987 Waddell, 1987, Inhibition of the localization of urethane in mouse tissues by ethanol, Food Chem. Toxicol., 25, 527, 10.1016/0278-6915(87)90204-3 Walker, 1974, Gas chromatographic analysis of urethane (ethyl carbamate) in wine, J. Agric. Food Chem., 22, 944, 10.1021/jf60196a007 Wasserfallen, 1987, Gaschromatographische Bestimmung von Urethan in Branntweinen und Brennereirohstoffen, Z. Lebensm. Unters. Forsch., 184, 392, 10.1007/BF01126665 1980 Weder, 1984, Studies on proteins and amino acids exposed to supercritical carbon dioxide extraction conditions, Food Chem., 15, 175, 10.1016/0308-8146(84)90002-5 Weder, 1989, Extraktion von Lebensmitteln mit überkritischem Kohlendioxid, 43, 105 Werner, 1947, Study of the polymerisation of cyanic acid, with special reference to dicyanic acid, 24, 209 Wikman-Coffelt, 1976, Radioimmunoassay method for analysis of ethylcarbamate in wine, Am. J. Enol. Vitic., 27, 115 Wucherpfennig, 1987, Beitrag zur Entstehung des Ethylcarbamats in alkoholischen Getränken auf der Basis der Sauerkirsche ‘Maraska’, Dtsch. Lebensm. Rdsch., 83, 344 Würdig, 1988, Bestimmung des Gehaltes an freiem und gesamtem Cyanwasserstoff im Wein, Wein-Wissenschaft, 43, 27 Yamamoto, 1988, Inhibition of the metabolism of urethane by ethanol, Drug Metab. Disp., 16, 355 Zimmerli, B., A. Alt and O. Zoller (1990) Unpublished results. Zimmerli, 1986, Occurrence and formation of ethyl carbamate (urethane) in fermented foods, 243 Zoller, 1990