Bauer-Marinovic M., Taugner F., Florian S., Glatt H.: Toxicity studies with 5-hydroxymethylfurfural and its metabolite 5-sulphooxymethylfurfural in wild-type mice and trans-genic mice expressing human sulphotransferases 1A1 and 1A2. Arch. Toxicol., 2012; 86: 701–711
Chan P.C., Hill G.D., Kissling G.E., Nyska A.: Toxicity and carcinogenicity studies of 4-methylimidazole in F344/N rats and B6C3F1 mice. Arch. Toxicol., 2008; 82: 45–53
Durling L.J., Busk L., Hellman B.E.: Evaluation of the DNA damaging effect of the heat-induced food toxicant 5-hydroxymethylfurfural (HMF) in various cell lines with different activities of sulfotransferases. Food Chem. Toxicol., 2009; 47: 880–884
Elsinghorst P.W., di Salvo M.L., Parroni A., Contestabile R.: Inhibition of human pyridoxal ki-nase by 2-acetyl-4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl) imidazole (THI). J. Enzyme Inhib. Med. Chem., 2015; 30: 336–340
Elsinghorst P.W., Raters M., Dingel A., Fischer J., Matissek R.: Synthesis and application of 13C-labeled 2-acetyl-4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl) imidazole (THI), an immunosuppressant observed in caramel food colorings. J. Agric. Food Chem., 2013; 61: 7494–7499
European Food Safety Authority (EFSA): Scientific opinion on the re-evaluation of caramel colours (E 150 a,b,c,d) as food additives. EFSA J., 2011; 9: 2004
Fierens T., Van Holderbeke M., Cornelis C., Jacobs G., Sioen I., De Maeyer M., Vinkx C., Vanermen G.: Caramel colour and process contaminants in foods and beverages: Part II – Occurrence data and exposure assessment of 2-acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole (THI) and 4-methylimidazole (4-MEI) in Belgium. Food Chem., 2018; 255: 372–379
Folmer D.E., Doell D.L., Lee H.S., Noonan G.O., Carberry S.E.: A U.S. population dietary exposure assessment for 4-methylimidazole (4-MEI) from foods containing caramel colour and from formation of 4-MEI through the thermal treatment of food. Food Addit. Contam. Part A Chem. Anal. Control. Expo. Risk Assess., 2018; 35: 1890–1910
Gobin S.J., Phillips J.A.: Immunosuppressive effects of 2-acetyl-4-tetrahydroxybutyl imidazole (THI) in the rat. Clin. Exp. Immunol., 1991; 85: 335–340
Hengel M., Shibamoto T.: Carcinogenic 4(5)-methylimidazole found in beverages, sauces, and caramel colors: Chemical properties, analysis, and biological activities. J. Agric. Food Chem., 2013; 61: 780–789
Houben G.F, Abma P.M., van den Berg H., van Dokkum W., van Loveren H., Penninks A.H., Seinen W., Spanhaak S., Vos J.G., Ockhuizen T.: Effects of the colour additive caramel colour III on the immune system: A study with human volunteers. Food Chem. Toxicol., 1992; 30: 749–757
Houben G.F., van den Berg H., Kuijpers M.H., Lam B.W., van Loveren H., Seinen W., Penninks A.H.: Effects of the color additive caramel color III and 2-acetyl-4 (5)-tetrahydroxybutylimidazole (THI) on the immune system of rats. Toxicol. Appl. Pharmacol., 1992; 113: 43–54
Houben G.F., van Dokkum W., van Loveren H., Penninks A.H., Seinen W., Spanhaak S., Ockhuizen T.: Effects of caramel colour III on the number of blood lymphocytes: A human study on caramel colour III immunotoxicity and a comparison of the results with data from rat studies. Food Chem. Toxicol., 1992; 30: 427–430
IARC Working Group on the Evaluation of Carcinogenic Risks to Humans: 4-Methylimidazole. W: Some Chemicals Present in Industrial and Consumer Products, Food and Drinking-Water. International Agency for Research on Cancer. Lyon 2013 447–459
Jang H.W., Jiang Y., Hengel M., Shibamoto T.: Formation of 4(5)-methylimidazole and its pre-cursors, α-dicarbonyl compounds, in Maillard model systems. J. Agric. Food Chem., 2013; 61: 6865–6872
Kim T.R., Kim S.U., Shin Y., Kim J.Y., Lee S.M., Kim J.H.: Determination of 4-methylimidazole and 2-acetyl-4()-tetrahydroxybutylimidazole in caramel color and processed foods by LC-MS/MS. Prev. Nutr. Food Sci., 2013; 18: 263–268
Kowalski S, Lukasiewicz M, Duda-Chodak A, Zięć G.: 5-Hydroxymethyl-2-furfural (HMF) – heat-induced formation, occurrence in food and biotransformation – a review. Pol. J. Food Nutr. Sci., 2013; 63: 207–225
Lee K.G., Jang H., Shibamoto T.: Formation of carcinogenic 4 (5)-methylimidazole in caramel model systems: A role of sulphite. Food Chem., 2013; 136: 1165–1168
Lee Y.C., Shlyankevich M., Jeong H.K., Douglas J.S., Surh Y.J.: Bioactivation of 5-hydroxymethyl-2-furaldehyde to an electrophilic and mutagenic allylic sulfuric acid ester. Biochem. Biophys. Res. Commun., 1995; 209: 996–1002
Mateo-Fernández M., Alves-Martínez P., Del Río-Celestino M., Font R., Merinas-Amo T., Alonso-Moraga Á.: Food safety and nutraceutical potential of caramel colour class IV using in vivo and in vitro assays. Foods, 2019; 8: 392
Monien B.H., Frank H., Seidel A., Glatt H.: Conversion of the common food constituent 5-hydroxymethylfurfural into a mutagenic and carcinogenic sulfuric acid ester in the mouse in vivo. Chem. Res. Toxicol., 2009; 22: 1123–1128
National Toxicology Program, US Department of Health and Human Services, Public Health Service, National Institutes of Health: NTP technical report on the toxicity studies of 2- and 4-Methylimidazole (CAS No. 693-98-1 and 822-36-6) administered in feed to F344/N rats and B6C3F1 mice. Toxic. Rep. Ser., 2004; 67: 1–G12
National Toxicology Program: Toxicology and carcinogenesis studies of 4-methylimidazole (Cas No. 822-36-6) in F344/N rats and B6C3F1 mice (feed studies). Natl. Toxicol. Program Tech. Rep. Ser., 2007; 535: 1–274
Norizadeh Tazehkand M., Topaktas M., Yilmaz M.B.: Assessment of chromosomal aberration in the bone marrow cells of Swiss Albino mice treated by 4-methylimidazole. Drug Chem. Toxicol., 2016; 39: 307–311
Ohtoyo M., Machinaga N., Inoue R., Hagihara K., Yuita H., Tamura M., Hashimoto R., Chiba J., Muro F., Watanabe J., Kobayashi Y., Abe K., Kita Y., Nagasaki M., Shimozato T.: Component of caramel food coloring, THI, causes lymphopenia indirectly via a key metabolic intermediate. Cell Chem. Biol., 2016; 23: 555–560
Ohtoyo M., Tamura M., Machinaga N., Muro F., Hashimoto R.: Sphingosine 1-phosphate lyase inhibition by 2-acetyl-4-(tetrahydroxybutyl) imidazole (THI) under conditions of vitamin B6 deficiency. Mol. Cell. Biochem., 2015; 400: 125–133
Reproductive and Cancer Hazard Assessment Branch Office of Environmental Health Hazard Assessment (OEHHA), California Environmental Protection Agency: No significant risk level (NSRL) for the proposition 65 carcinogen 4-methylimidazole. 2011 https://oehha.ca.gov/media/downloads/crnr/010711nsrlrisk4ei.pdf
Rozporządzenie Komisji (UE) nr 231/2012 z dnia 9 marca 2012 r. ustanawiające specyfikacje dla dodatków do żywności wymienionych w załącznikach II i III do rozporządzenia (WE) nr 1333/2008 Parlamentu Europejskiego i Rady (Dz.U. L 83 z 22.3.2012, s. 1)
Rozporządzenie Parlamentu Europejskiego i Rady (WE) nr 1333/2008 z dnia 16 grudnia 2008 r. w sprawie dodatków do żywności (Dz.U. L 354 z 31.12.2008, s. 16)
Selim S., Chappel C.I., Schoenig G.P.: Absorption, distribution and excretion of the colour fraction of caramel colour IV in the rat. Food Chem. Toxicol., 1992; 30: 445–451
Suiko M., Kurogi K., Hashiguchi T., Sakakibara Y., Liu M.C.: Updated perspectives on the cytosolic sulfotransferases (SULTs) and SULT-mediated sulfation. Biosci. Biotechnol. Biochem., 2017; 81: 63–72
Surh Y.J., Liem A., Miller J.A., Tannenbaum S.R.: 5-Sulfooxy-methylfurfural as a possible ul-timate mutagenic and carcinogenic metabolite of the Maillard reaction product, 5-hydroxy-methylfurfural. Carcinogenesis, 1994; 15: 2375–2377
Surh Y.J., Tannenbaum S.R.: Activation of the Maillard reaction product 5-(hydroxymethyl)furfural to strong mutagens via allylic sulfonation and chlorination. Chem. Res. Toxicol., 1994; 7: 313–318
Wang L., Ren B., Liu Y., Lu Y., Chang F., Yang L.: 2-acetyl-4-tetrahydroxybutylimidazole and 4-methylimidazole in caramel colours, vinegar, and beverages in China. Food Addit. Contam. Part B Surveill., 2015; 8: 163–168
Yamaguchi H., Masuda T.: Determination of 4(5)-methylimidazole in soy sauce and other foods by LC-MS/MS after solid-phase extraction. J. Agric. Food Chem., 2011; 59: 9770–9775
Yu P., Xu X.B., Yu S.J.: Comparative study of the effect of glucosamine and free ammonium on 4-methylimidazole formation. J. Agric. Food Chem., 2015; 63: 8031–8036
Zhou Z, Hu X, Hong X, Zheng J, Liu X, Gong D, Zhang G.: Interaction characterization of 5-hydroxymethyl-2-furaldehyde with human serum albumin: Binding characteristics, conformational change and mechanism. J. Mol. Liq., 2020; 297: 111835