4-methylimidazole
Structural formula | ||||||||||||||||||||||
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General | ||||||||||||||||||||||
Surname | 4-methylimidazole | |||||||||||||||||||||
other names |
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Molecular formula | C 4 H 6 N 2 | |||||||||||||||||||||
Brief description |
light yellow solid |
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properties | ||||||||||||||||||||||
Molar mass | 82.10 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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density |
1.0416 g cm −3 |
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Melting point |
46-48 ° C |
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boiling point |
263 ° C |
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solubility |
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Refractive index |
1.5037 (14 ° C) |
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safety instructions | ||||||||||||||||||||||
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Toxicological data | ||||||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
4-Methylimidazole (4-MEI for short) is a heterocyclic organic compound from the group of imidazoles with the empirical formula C 4 H 6 N 2 .
Occurrence
4-Methylimidazole can be produced during fermentation or browning of food by the Maillard reaction . It occurs in ammonia caramel (E 150c) because it is a by-product of its manufacture. Since caramel is also used as a coloring in cola, it is a controversial ingredient there.
Extraction and presentation
4-Methylimidazole is synthesized by the reaction of methylglyoxal with ammonia and formaldehyde in the Radziszewski synthesis .
use
4-methylimidazole is an important intermediate in the manufacture of pharmaceutical products. It is the starting material for drugs and antiseptic agents, as well as for photo developer fluid .
toxicity
4-methylimidazole can cause convulsions in rabbits, mice and chickens. A carcinogenic effect was also found in rats and mice.
Individual evidence
- ↑ a b c d e f g h Entry on 4-methylimidazole in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
- ↑ a b c d Entry on 4-Methylimidazole in the Hazardous Substances Data Bank , accessed July 27, 2012.
- ↑ Michael F. Jacobson: Petition to Bar the Use of Caramel Colorings Produced With Ammonia and Containing the Carcinogens 2-Methylimidazole and 4-Methylimidazole (PDF; 97 kB) Center for Science in the Public Interest . 2011. Retrieved January 11, 2011.
- ↑ a b PC Chan, GD Hill, GE Kissling, A. Nyska: Toxicity and carcinogenicity studies of 4-methylimidazole in F344 / N rats and B6C3F1 mice . In: Arch Toxicol . tape 82 , no. 1 , 2008, p. 45-53 , PMID 17619857 .
- ↑ Proportion of controversial cola in cola varies by country . n-tv.de, July 28, 2012, accessed on May 11, 2013.
- ↑ Patent US4377696 : Preparation of 4-methylimidazoles. Published on March 22, 1983 , applicant: BASF Aktiengesellschaft, inventor: Fritz Graf.