4-methylimidazole

Structural formula
General
Surname	4-methylimidazole
other names	4-methyl-1 H -imidazole; 5-methyl-1 H -imidazole; 4 (5) -methylimidazole; 4-MEI;
Molecular formula	C 4 H 6 N 2
Brief description	light yellow solid
External identifiers / databases
EC number	212-497-3
ECHA InfoCard	100.011.361
PubChem	13195
ChemSpider	12640
DrugBank	DB03385
Wikidata	Q230021
properties
Molar mass	82.10 g mol −1
Physical state	firmly
density	1.0416 g cm −3
Melting point	46-48 ° C
boiling point	263 ° C
solubility	soluble in water; very soluble in ethanol;
Refractive index	1.5037 (14 ° C)
safety instructions
H and P phrases	H: 302 + 312-314
	P: 280-305 + 351 + 338-310
Toxicological data	751 mg kg −1 ( LD 50 , rat , oral )
	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. ‌

[GESTIS-1] ↑ ^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) .

[toxnet-2] Entry on 4-Methylimidazole in the Hazardous Substances Data Bank , accessed July 27, 2012.

[Petition-3] 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.

[nih-4] 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 .

[web-5] Proportion of controversial cola in cola varies by country . n-tv.de, July 28, 2012, accessed on May 11, 2013.

[basf-6] Patent US4377696 : Preparation of 4-methylimidazoles. Published on March 22, 1983 , applicant: BASF Aktiengesellschaft, inventor: Fritz Graf. ‌