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199885

Sigma-Aldrich

4(5)-Methylimidazole

98%

Synonym(s):

1H-4-Methylimidazole, 4(or 5)-Methylimidazole, 4-Methyl-1H-imidazole, 4-Methylimidazole, 5-Methyl-1H-imidazole, 5-Methylimidazole

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About This Item

Empirical Formula (Hill Notation):
C4H6N2
CAS Number:
822-36-6
Molecular Weight:
82.10
Beilstein:
1453
EC Number:
212-497-3
MDL number:
MFCD00005201
UNSPSC Code:
12352005
PubChem Substance ID:
24851942
NACRES:
NA.22

Quality Level

100

Assay

98%

bp

263 °C (lit.)

mp

44-47 °C (lit.)

solubility

H2O: soluble, clear, colorless to yellow (50 mg/mL)

SMILES string

Cc1c[nH]cn1

InChI

1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)

InChI key

XLSZMDLNRCVEIJ-UHFFFAOYSA-N

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General description

4(5)-Methylimidazole was quantified in coffee by GC-MS method.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312,H314

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

314.6 °F - closed cup

Flash Point(C)

157 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Joon-Kwan Moon et al.
Journal of agricultural and food chemistry, 59(2), 615-618 (2010-12-29)
4(5)-Methylimidazole has received the attention of federal and state regulatory agencies because of its carcinogenicity and common presence in foods and beverages. In the present study, the formation of 4(5)-methylimidazole in Maillard reaction model systems consisting of D-glucose/NH(3), L-rhamnose/NH(3), methylglyoxal/NH(3)
Hitomi Yamaguchi et al.
Journal of agricultural and food chemistry, 59(18), 9770-9775 (2011-09-02)
A method for the determination of 4(5)-methylimidazole (4MeI) in naturally brewed soy sauce was developed for the first time using solid-phase extraction (SPE) and liquid chromatography-tandem mass spectrometry (LC-MS/MS). SPE on silica-based reversed-phase cartridges with heptafluorobutyric acid as an ion-pairing
Young-Teck Kim et al.
Talanta, 78(3), 998-1003 (2009-03-10)
Based on the principle of liquid core waveguide, a novel microfluidic device with micro-scale detection window capable of sensing flashlight emitted from rapid 1,1'-oxalyldi-4-methylimidazole (OD4MI) chemiluminescence (CL) reaction was fabricated. Light emitted from OD4MI CL reaction occurring in the micro-dimensional
Matt Hengel et al.
Journal of agricultural and food chemistry, 61(4), 780-789 (2013-01-09)
Since the National Toxicology Program (NTP) identified 4(5)-methylimidazole [4(5)-MI] as a cancer causing chemical in 2007 and the State of California added it to the Proposition 65 list of compounds as a carcinogen on January 7, 2011, many researchers and
Cédric Moretton et al.
Journal of agricultural and food chemistry, 59(8), 3544-3550 (2011-03-09)
4-Methylimidazole (4MeI) is a nitrogen compound formed during the manufacture of class III and IV caramel colors. The European Commission has limited its content to 250 ppm. Two methods were compared to perform 4MeI quantification in caramels. The first one
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