1998
DOI: 10.1021/jf9710239
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Ammoniated Forage Poisoning:  Isolation and Characterization of Alkyl-Substituted Imidazoles in Ammoniated Forage and in Milk

Abstract: A study has been performed to isolate and identify toxic nitrogen-containing compounds in ammoniated forages and in milk samples from sheep and a cow fed with ammoniated forages. Together with two previously identified imidazoles, 4-methylimidazole and 2-methylimidazole, the following imidazoles were isolated:  1,2-dimethyl-, 1,4-dimethyl-, 1,5-dimethyl-, 2,4-dimethyl-, and 2-ethyl-4-methylimidazole. The imidazoles were identified with gas chromatography/mass spectrometry and gas chromatography with nitrogen−p… Show more

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Cited by 15 publications
(4 citation statements)
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References 13 publications
(28 reference statements)
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“…Ammoniation can involve application of liquid or anhydrous ammonia or result from application of urea, or use of the ammonia-fiber expansion (AFEX) technology. Though ammonia treatment improves the nutritive value of low-quality forages, feeding ammoniated forage may induce acute toxicity in ruminants because of potential deleterious effects on the central nervous system by causing crazy cow syndrome or bovine bonkers (Muller et al, 1998). This is because ammoniation of high-quality forages such as alfalfa and small grain hays predisposes animals to consumption of the toxic compound 4-metylimidazol, produced after interaction of ammonia with reducing sugars (Jung and Allen, 1995;Muller et al, 1998).…”
Section: Alkali Treatmentmentioning
confidence: 99%
“…Ammoniation can involve application of liquid or anhydrous ammonia or result from application of urea, or use of the ammonia-fiber expansion (AFEX) technology. Though ammonia treatment improves the nutritive value of low-quality forages, feeding ammoniated forage may induce acute toxicity in ruminants because of potential deleterious effects on the central nervous system by causing crazy cow syndrome or bovine bonkers (Muller et al, 1998). This is because ammoniation of high-quality forages such as alfalfa and small grain hays predisposes animals to consumption of the toxic compound 4-metylimidazol, produced after interaction of ammonia with reducing sugars (Jung and Allen, 1995;Muller et al, 1998).…”
Section: Alkali Treatmentmentioning
confidence: 99%
“…4‐MeI has been identified in caramel colors (Wilks and others ; Buckee and Bailey ; Fernandes and Ferreira ; Klejdus and others ; Moretton and others ; Yamaguchi and Masuda ; Schlee and others ; Petruci and others ) and in processed foods, such as coffee (Casal and others ; Klejdus and others ; Lojkoval and others ; Yamaguchi and Masuda ), soy sauce (Yamaguchi and Masuda ), beer (Klejdus and others ; Cunha and others ), carbonated beverages (Cunha and others ; Yamaguchi and Masuda ; Schlee and others ; Wang and Schnute ; Lim and Shin ), and milk (Muller and others ).…”
Section: Introductionmentioning
confidence: 99%
“…They have been based on liquid chromatography/ultraviolet light (LC/UV) and liquid chromatography-mass spectrometry (LC/MS) (Lawrence and Charbonneau 1987;Ding et al 1991;Moravcová et al 1992;Wagner et al 1993; Thomsen and Willumsen 1995;Mü ller et al 1998), capillary electrophoresis (Ong et al 1994), and gas chromatography with derivatization (Kröplien 1986;Fernandes and Ferreira 1997). Quantification of 4(5)-methylimidazole in coffee was performed via ion-pair extraction with bis-2-ethylhexylphosphate (BEHP), isobutylchloroformate derivatization and gas chromatography-mass spectrometry (Casal et al 2002).…”
Section: Introductionmentioning
confidence: 99%