Akrylaldehyd

• Autorzy: Sitarek K.

Warianty tytułu

EN

Acrylaldehyde

• Języki publikacji: PL

Abstrakty

PL

Akrylaldehyd jest bezbarwną cieczą o ostrym nieprzyjemnym zapachu. Dobrze rozpuszcza się w rozpuszczalnikach organicznych. Należy do substancji bardzo toksycznych, wartość LD50 dla szczurów po podaniu per os wynosi 46 mg/kg m.c., a wartość CL50 wynosi 750 mg/m3 po 10 min narażenia. Akrylaldehyd jest produktem pośrednim przy otrzymywaniu syntetycznego glicerolu, poliuretanu i żywic poliestrowych, metioniny, leków, herbicydów oraz kwasu akrylowego. Jest to związek o silnym działaniu drażniącym na błony śluzowe. Narażenie ludzi na akrylaldehyd o stężeniu 0,34 mg/m3 przez 10 min powoduje podrażnienie błon śluzowych, a o stężeniu 0,69 mg/m3 przez 40 min prowadzi u ludzi do zmniejszenia częstości oddechu, podrażnienia błon śluzowych i podrażnienia skóry szyi. Wartość RD50 dla myszy wynosi około 2 mg/m3, a dla szczurów 13,7 mg/m3. Przedłużone narażenie zwierząt na pary akrylaldehydu powoduje rozedmę płuc oraz zapalenie płuc, wątroby i nerek u małp, psów i świnek morskich. Czynników rakotwórczych dla zwierząt. Istnieją jednak dowody, że jego główny metabolit – aldehyd glicydowy jest rakotwórczy dla zwierząt. Akrylaldehyd jest mutagenny, może tworzyć addukty z makrocząsteczkami, a także indukować wady wrodzone u gryzoni. Związek ten dobrze wchłania się w układzie oddechowym, a wydala się z powietrzem wydychanym. Uwzględniając silne działanie drażniące akrylaldehydu, proponuje się przyjęcie stężenia 0,05 mg/m3 za wartość najwyższego dopuszczalnego stężenia (NDS), a stężenia 0,1 mg/m3 za wartość najwyższego dopuszczalnego stężenia chwilowego (NDSCh) oraz oznaczenie substancji literami „Sk” i „C”.

EN

Acrylaldehyde is a colourless to yellowish, flemmable liquid with a disagreeble, choking odour. It is used as an intermediate in the manufacture of synthetic glycerol, polyurethane and polyester resins, pharmaceuticals and herbicides, and as a tear gas. The oral LD50 in rats is 46 mg/kg, and the inhalation LC50 in rats is 750 mg/m3 (10 min of exposure) or 300 mg/m3 (30 min of exposure). Acrylaldehyde is intensely irritating to the eyes and upper respiratory tract. Liver and lungs metabolize this chemical. It is mutagenic in Salmonella typhimurium, produces adducts of bacterial DNA and is clastogenic for DNA of rat hepatocytes. The carcinogenic potential of acrylaldehyde per se has not been adequately determined, but glycidaldehyde, a potential its metabolite is considered to be carcinogenic. Acrylaldehyde is not classifiable as a human carcinogen. The Expert Group recommends a MAC of 0.05 mg/m3 for acrylaldehyde and according to its irritative effects – a MAC-STEL of 0.10 mg/m3. Because percutaneous absorption of acrylaldehyde has caused systemic toxicity in laboratory animals, “Sk” notation is considered appropriate. “C” – corrosive notation is also recommended.

Słowa kluczowe

PL

akrylaldehyd; NDS; NDSCh; narażenie zawodowe

EN

acrylaldehyde; MAC (TWA); MAC (STEL)

• Wydawca: Centralny Instytut Ochrony Pracy - Państwowy Instytut Badawczy
• Czasopismo: Podstawy i Metody Oceny Środowiska Pracy
• Rocznik: 2006
• Tom: Nr 2 (48)
• Strony: 5--30
• Opis fizyczny: Bibliogr. 105 poz., rys., tab.

Twórcy

autor

Sitarek K.

• Instytut Medycyny Pracy im. prof. dr. med. Jerzego Nofera 90-950 Łódź ul. św. Teresy 8

Bibliografia

• .ACGIH (2000). Documentation of the threshold limit values. Ed. 6, Cincinnati (supplement).
• 2.Andersen K.J. i in. (1972) Evaluation of herbicides for possible mutagenic properties. J. Agric. Food. Chem. 20, 649-656.
• 3.Au W. i in. (1980) Cytogenetic toxicity of cyclophosphamide and its metabolites in vitro. Cytogenet. Cell Genet. 26, 108-116.
• 4.Babiuk C. i in. (1985) Sensory irritation response to inhaled aldehydes after formaldehyde pretreatment. Toxicol. Appl. Pharmacol. 79, 143-149.
• 5.Basu A.K., Marnett L.J. (1984) Molecular requirements for the mutagenicity of malondialdehyde and related acroleins. Cancer Res. 44, 2848-2854.
• 6.Beauchamp R.O. i in. (1985) A critical review of the literature on acrolein toxicity. CRC Crit. Rev. Toxicol. 14, 309-380.
• 7.Ben-Dyke R. i in. (1970) Acute toxicity data for pesticides. World Rev. Respir. Dis. 133, 191-196.
• 8.Berrigan M.J. i in. (1980). Protection by N-acetylcysteine of cyclophosphamide metabolism – related in vivo depression of mixed function oxygenase activity and in vitro denaturation of cytochrome P – 450. Biochem. Biophys. Res. Commun. 93, 797-803.
• 9.Bouley G. i in. (1975) Effects of a weak dose of continuously inhaled acrolein in rats. Eur. J.Toxicol. 8, 291-297.
• 10.Carpenter C.P. i in. (1949) The assay of acute vapor toxicity, and the grading and interpretation of results on 96 chemical compounds. J. Ind. Hyg. Toxicol. 31, 343-346.
• 11.Catilina P. i in. (1966) Experimental respiratory lesions by inhalation of acrolein in the rat. Arch. Mal. Prof. Med. Trav. Secur. Soc. 27, 857-867.
• 12.Cheminfo (2002) [Komputerowa baza danych].
• 13.Chhibber G., Gilani S.H. (1986) Acrolein and embryogenesis: an experimental study. Environ. Res. 39, 44-49.
• 14.Chung F.L. i in. (1984) Formation of cyclic 1,N2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44, 990-995.
• 15.Claussen U. i in. (1980) The embryotoxicity of the cyclophosphamide metabolite acrolein in rabbits, tested in vivo by i.v. injection and by the yolk-sac method. Drug Res. 30, 2080-2083.
• 16.Cooper K.O. i in. (1987) Inhibition of microsomal cytochrome c reductase activity by a series of α,β- unsaturated aldehydes. Biochem. Pharmacol. 36, 627-631.
• 17.Costa D.L. i in. (1986) Altered lung function and structure in the rat after subchronic exposure to acrolein. Am. Rev. Respir. Dis. 133, 286-291.
• 18.Cox R. i in.. (1988) Inhibition of DNA methylase activity by acrolein. Carcinogenesis 9, 463-465.
• 19.Curren R.D. i in. (1988) Mutagenesis of xeroderma pigmentosum fibroblasts by acrrolein. Mutat. Res. 209, 17-22.
• 20.Darley E.F. i in. (1960) Plant damage and eye irritation from ozone-hydrocarbon reactions. J. Agric. Food Chem. 8, 483-485.
• 21.Davis T.R. i in. (1967) Mechanism of respiratory effects during exposure of guinea pigs to irritants. Arch. Environ. Health. 15, 412-419.
• 22.Dawydzik L. i in. (2001) Sprawozdanie z realizacji umowy nr IMP-6/01. Opracowanie w ujęciu tabelarycznym danych o narażeniu zawodowym w nadzorowanych przez inspekcję sanitarną zakładach pracy w 2000 roku. Łódź, Instytut Medycyny Pracy.
• 23.Debethizy J.D. (1987) The disposition and metabolism of acrylic acid and ethyl acrylate in male Sprague-Dawley rats. Fundam. Appl. Pharmacol. 8, 549-561.
• 24.Draminski W. i in. (1983) A new pathway of acrolein metabolism in rats. Arch. Toxicol. 52, 243-247. Dziennik Ustaw Rzeczypospolitej Polskiej. nr 217, poz. 1833 z dnia 29 listopada 2002 r.
• 25.Rozporządzenie ministra pracy i polityki socjalnej w sprawie najwyższych dopuszczalnych stężeń i natężeń czynników szkodliwych dla zdrowia w środowisku pracy Dziennik Ustaw Rzeczypospolitej Polskiej nr 201, poz. 1674 z dnia 14 października 2005 r Załącznik do Rozporządzenie ministra zdrowia z dnia 28 września 2005 r. w sprawie wykazu substancji niebezpiecznych wraz z ich klasyfikacją i oznakowaniem
• 26.Egle J.L. (1972) Retention off inhaled formaldehyde, propionaldehyde, and acrolein in the dog. Arch. Environ. Health. 25, 119-124.
• 27.Ellenberger J., Mohn G.R. (1976) Comparative mutagenicity testing of cyclophosphamide and some of its metabolites. Mutat. Res. 37, 120 (abstract).
• 28.Ellenberger J., Mohn G.R. (1977) Mutagenic activity of major mammalian metabolites of cyclophosphamide toward several genes of Escherichia coli. J. Toxicol. Environ. Health. 3, 637-650.
• 29.EPA (1986) Health Assessment Document for Acrolein. US EPA, EPA-600/8-86-014A
• 30.Epstein S.S. I Shafner H. (1968). Chemical mutagens in human environment. Nature (Lond.) 219, 385-387.
• 31.Feron V.J., Kruysse A. (1977) Effects of exposure to acrolein vapor in hamsters simultaneously treated with benzo[a]pyrene or diethylnitrosamine. J. Toxicol. Environ. Health. 3, 379-394.
• 32.Feron V.J. i in. (1978) Repeated exposure to acrolein vapour: subacute studies in hamsters, rats and rabbits. Toxicology. 9, 47-57.
• 33.Florin I. i in. (1980) Screening of tobacco smoke constituents for mutagenicity using the Ames” test. Toxicology 18, 219-232.
• 34.Foiles P.G. i in. (1989) Application of an immunoassay for cyclic acrolein deoxyguanosine adducts to assess their formation in DNA of Salmonella typhimurium under conditions of mutation induction by acrolein. Carcinogenesis 10, 87-90.
• 35.Galloway S.M. i in. (1987) Chromosome aberrations and sister chromatid exchanges in Chinese hamster ovary cells: evaluations of 108 chemicals. Environ. Mol. Mutagen. 10 (supplement), 1-175.
• 36.Green M.A., Egle J.L. (1983) The effects of acetaldehyde and acrolein on blood pressure in guanethidine-pretreated hypertensive rats. Toxicol. Appl. Pharmacol. 69, 29-36.
• 37.Gurtoo H.L. i in. (1981a) Role of glutathione in the metabolism-dependent toxicity and chemotherapy of cyclophosphamide. Cancer Res. 41, 3584-3591.
• 38.Gurtoo H.L. i in. (1981b) Studies on the mechanism of denaturation of cytochrome P-450 by cyclophosphamide and its metabolites. J. Biol. Chem. 256, 11691-11701.
• 39.Hales B.F. (1982) Comparison of the mutagenicity and teratogenicity of cyclophosphamide and its metabolites, 4-hydroxycyclophosphamide, phosphoramide mustard, and acrolein. Cancer Res. 42, 3016-3021.
• 40.Haworth S. i in. (1983) Salmonella mutagenicity test results for 250 chemicals. Environ. Mutagen. Suppl. 1, 3-142.
• 41.Hemminki K i in. (1980) Comparison of alkylation rates and mutagenicity of directly acting industrial and laboratory chemicals. Arch. Toxicol. 46, 277-285.
• 42.Hoffman C. i in. (1989) Detection of acrolein congener-DNA adducts isolated from cellular systems. Arch. Toxicol. Suppl. 13, 219-223.
• 43.Hovding G. (1969) Occupational dermatitis from pyrolysis products of polythene. Acta Dermatovenereol. 49, 147-149.
• 44.IARC (1985) Monographs on the evaluation of the carcinogenic risk of chemicals to humans. Lyon, WHO 36, 133-161.
• 45.IPCS (1991) Acrolein health and safety guide. Geneva, WHO.
• 46.IPCS (1992) Environmental Health Criteria 127. Acrolein. Geneva, WHO.
• 47.Izard C. (1973) Effects de I´acroléine sur la division cellulaire, le cycle et la synthése de I´ADN, chez Vicia faba. C. R. Acad. Sci. Paris Ser. D. 276, 1745-1747.
• 48.Kane L.E., Alarie Y. (1978) Evaluation of sensory irritation from acrolein-formaldehyde mixtures. Am. Ind. Hyg. Assoc. J. 39, 270-274.
• 49.Kane L.E., Alarie Y. (1979) Interactions of sulfur dioxide and acrolein as sensory irritants. Toxicol. Appl. Pharmacol. 48, 305-315.
• 50.Kankaanpaa J. i in. (1979) Embryotoxicity of acrolein, acrylamide in developing chick embryos. Toxicol. Lett. 4, 93-96.
• 51.Kaye C.M. (1973) Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein. Biochem. J. 134, 1093-1101.
• 52.Khudoley V.V. i in. (1986) Evaluation of mutagenic activity of carcinogenes and other chemical agents with Salmonella typhimurium assays. Vopr. Onkol. 32, 72-80 (in Russian).
• 53.Korhonen A. i in. (1983) Embryotoxic effects of acrolein, methyacrylates, guanidines and resorcinol on three day chicken embryos. Acta Pharmacol. Toxicol. 52, 95-99.
• 54.Kutzman R.S. i in. (1982a) A subchronic acrolein inhalation study in rats. IV. Impact on hypertensionsensitive and resistant animals (abstract nr 573). Toxicologist. 2, 163.
• 55.Kutzman R.S. i in. (1982b) A subchronic acrolein inhalation study in rats. I. Biochemical and pathologic changes (abstract nr 570). Toxicologist. 2, 162.
• 56.Kutzman R.S. i in. (1982c) The biodistribution and metabolic fate of [11C]-acrylic acid in the rat after acute inhalation exposure or stomach intubation. J. Toxicol. Environ. Health. 10, 969-979.
• 57.Lam C.W. i in. (1985) Depletion of nasal mucosal glutathione by acrolein and enhancement of formaldehyde-induced DNA-protein cross-linking by simultaneous exposure to acrolein. Arch. Toxicol. 58, 67-71.
• 58.Le Bouffant L. i in. (1980) Action of intensive cigarette smoke inhalations on the rat lung. Role of particulate and gaseous cofactors. J. Natl. Cancer Inst. 64, 273-281.
• 59.Leach C.L. i in. (1987) The pathologic and immunologic effects of inhaled acrolein in rats. Toxicol. Lett. 39, 189-198.
• 60.Leonardos G. i in. (1969) Odor threshold determinations of 53 odorant chemicals. J. Air Poout. Control Assoc. 19, 91-95.
• 61.Lijinsky W., Reuber M.D. (1987) Chronic carcinogenesis studies of acrolein and related compounds. Toxicol. Ind. Health. 3, 337-345.
• 62.Lijinsky W., Andrews A.W. (1980) Mutagenicity of vinyl compounds in Salmonella typhimurium. Teratogen. Carcinogen. Mutagen. 1, 259-267.
• 63.Loquet C. i in. (1981) Studies on mutagenic constituents of apple brandy and various alcoholic beverages collected in Western France, a high incidence area for oesophageal cancer. Mutat. Res. 88, 155-164.
• 64.Lutz D. i in. (1982) Structure-mutagenicity relationship in ,-unsaturated carbonylic compounds and their corresponding allylic alcohols. Mutat. Res. 93, 305-315.
• 65.Lyon J.P. i in. (1970) Repeated and continuous exposure of laboratory animals to acrolein Toxicol. Appl. Pharmacol. 17, 726-732.
• 66.Marinello A.J. i in. (1978) Denaturation of cytochrome p-450 by cyclophosphamide metabolites. Biochem. Biophys. Res. Commun. 83, 1347-1353.
• 67.Marinello A.J. i in. (1984) Metabolism and binding of cyclophosphamide and its metabolite acrolein to rat hepatic microsomal cytochrome P-450. Cancer Res. 44, 4615-4621.
• 68.Marnett L.J. i in. (1985) Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA 104. Mutat. Res. 148, 25-34.
• 69.Munsch N. i in. (1973) Effects of acrolein on DNA synthesis in vitro. Fed. Eur. Biochem. Soc. Lett. 30, 286-289.
• 70.Munsch N. i in. (1974a) Incorporation d`acroleine 3H dans le foie du rat et chez Dunaliella bioculata. Biochimie 56, 1433-1436.
• 71.Munsch N. i in. (1974b) In vitro binding of 3H-acrolein to regenerating rat liver DNA polymerase. Experientia 30,1234-1236.
• 72.Murphy S.D. i in. (1963) Respiratory response of guinea pigs during acrolein inhalation and its modification by drugs. J. Pharmacol. Exp. Ther. 141, 79-83.
• 73.Patel J.M. i in. (1980) The biotransformation of allyl alcohol and acrolein in rat liver and lung preparations. Drug. Metab. Disposal. 8, 305-308.
• 74.Philippin Cl. i in. (1969). Physiological effect of acrolein on the mouse. Praeventivmedizin. 14, 317- 318.
• 75.Plotnikova M.M. (1957) Data on hygienic evaluation of acrolein as a pollution of the atmosphere. Gig. I Sanit. 22(6), 10-15 (in Russian).
• 76.Rapoport I.A. (1948) Mutates under the influence of unsaturated aldehydes. Dokl. Akad. Nauk. SSSR. 16, 713-715 (in Russian).
• 77.Rikans L.E. (1987) The oxidation of acrolein by rat liver aldehyde dehydrogenases. Relation to allyl alcohol hepatoxicity. Metab. Disposal 15, 356-362.
• 78.Salaman M.H., Roe F.J.C. (1956) Further testes for tumour-initiating activity: N,N,-di-(2-chloroethyl)- p-aminophenylbutyric acid (CB1348) as an initiator of skin tumour formation in the mouse. Br. J. Cancer. 10, 363-378.
• 79.Salem H., Cullumbine H. (1960) Inhalation toxicities of some aldehydes. Toxicol. Appl. Pharmacol. 2, 183-187.
• 80.Schielke D.J. (1987) Gasterectomy following a rare caustic lesion. Chirurg 58, 50-52 (in German).
• 81.Shamberger R.J. i in. (1974) Antioxidants and cancer. IV. Initiating activity of malonaldehyde as a carcinogen. J. Natl. Cancer Inst. 53, 1771-1773.
• 82.Shapiro R. i in. (1986) Reactions of nucleosides with glyoxal and acrolein. W: The role of cyclic nucleic acid adducts in carcinogenesis and mutagenesis. Proceedings of a meeting organized by the JARC and co-sponsored by the US National Cancer Institute, and Lawrence Berkely Laboratory at the University of California. Lyon, 17-19 September, Lyon International Agency for Research on Cancer 165-173 (IARC Scientific Publications no. 70). Shell Chemical Corporation (1957) Toxicity data sheet SC57-76, “Acrolein”.
• 83.Sim V.M., Pattle R.E. (1957) Effect of possible smog irritants on human subjects. J. Am. Med. Assoc. 165, 1908-1913.
• 84.Sinkuvene D. (1970) Hygienic assessment of acrolein as an atmospheric pollutant. Gig. i Sanit. 35(3), 6-10 (in Russian).
• 85.Skog E. A. (1950) Toxicological investigation of lower aliphatic aldehydes. I. Toxicity of formaldehyde, acetaldehyde, propionaldehyde and butyraldehyde, as well as of acrolein and crotonaldehyde. Acta Pharmacol. 6, 299-318.
• 86.Slott V.L., Hales B.F. (1985) Teratogenicity and embryolethality of acrolein and structurally related compounds in rats. Teratology 32, 65-72.
• 87.Slott V.L., Hales B.F. (1986) The embryolethality and teratogenicity of acrolein in cultured rat embryos. Teratology. 34, 155-163.
• 88.Slott V.L., Hales B.F. (1987a) Enhancement of the embryotoxicity of acrolein, but not phosphoramide mustard, by glutathione depletion in rat embryos in vitro. Biochem. Pharmacol. 36, 2019-2025.
• 89.Slott V.L., Hales B.F. (1987b) Protection of rat embryos in culture against the embryotoxicity of acrolein using exogenous glutathione. Biochem. Pharmacol. 36, 2087-2194.
• 90.Smith R.A. i in. (1990) Acrolein mutagenicity in the V79 assay. Carcinogenesis. 11, 497-498.
• 91.Smyth H.F. Jr. i in. (1951) Range-finding toxicity data, list IV. Arch. Ind. Hyg. Occup. Med. 4, 119- 122.
• 92.Sprince H. i in. (1979) Comparison of protection by L-ascorbic acid, L-cysteine, and adrenergicblocking agents against acetaldehyde, acrolein, and formaldehyde toxicity: implications in smoking. Agents Actions. 9, 407-414.
• 93.Stahlmann R. i in. (1985) Effects of the cyclophosphamide metabolite acrolein in mammalian limb bud cultures. Arch. Toxicol. 57, 163-167.
• 94.Steinhagen W.H., Barrow C.S. (1984). Sensory irritation structure-activity study of inhaled aldehydes in B6C3F1 and Swiss-Webster mice. Toxicol. Appl. Pharmacol. 72, 495-503.
• 95.Stephens E.R. i in. (1961) Photochemical reaction products in air pollution. Int. J. Air Water Pollut. 4, 79-100.
• 96.Toxicological profile for acrolein (1990) U.S. Department of Health and Human Services. Public Health Service. Agency for Toxic Substances and Disease Registry.
• 97.Van Duuren B.L. i in. (1965) Carcinogenicity of epoxides, lactones and peroxy compounds. II. J. Natl. Cancer Inst. 35, 707-717.
• 98.Van Duuren B.L. i in. (1966) Carcinogenicity of epoxides, lactones, and peroxy compounds. IV. Tumor response in epithelial and connective tissue in mice and rats. J. Natl. Cancer Inst. 37, 825-838.
• 99.Van Duuren B.L. i in. (1967a) Carcinogenicity of epoxides, lactones, and peroxy compounds. VI. Structure and carcinogenic activity. J. Natl. Cancer Inst. 39, 1217-1228.
• 100.Van Duuren B.L. i in. (1967b) Carcinogenicity of epoxides, lactones, and peroxy compounds. V. Subcutaneous injection in rats. J. Natl. Cancer Inst. 39, 1213-1216.
• 101.Van Eick A.J. (1977) The effect of acrolein in air on the eye blinking frequency of man and guinea pig. Rijswijk, The Netherlands, Technical and Physical Research, Medical Biological Laboratory, TNOMBL (Report No. A76/K/098).
• 102.Watanabe T., Aviado D.M. (1974) Functional and biochemical effects on the lung following inhalation of cigarette smoke and constituents. II. Skatole, acrolein, and acetaldehyde. Toxicol. Appl. Pharmacol. 30, 201-209.
• 103.Weber-Tschopp A. i in. (1977) Experimental irritation by acrolein in human beings. Z. Arbeitswiss. 32, 166-171 (in German).
• 104.Wilmer J.L. i in. (1986) Attenuation of cytogenetic damage by 2-mercaptoethane-sulphonate in cultured human lymphocytes exposed to cyclophosphamide and its reactive metabolites. Cancer Res. 46, 203-210.
• 105.Zimmering S. i in. (1985) Chemical mutagenesis testing in Drosophila II. Results of 20 coded compounds tested for the National Toxicology Program. Environ. Mutagen. 7, 87-100.