DETERMINATION OF 2,6-DI-TERT-BUTYLHYDROXYBENZENE IN A CHEMICAL-TOXICOLOGICAL INVESTIGATION OF BIOLOGICAL MATERIAL

DOI: https://doi.org/None
Issue: 
5
Year: 
2017

E.P. Tsatsua (1), A.P. Astashkina (2), PhD; Professor V.K. Shormanov (1), PhD; M.V. Rymarova (1), PhD; A.O. Kvasova (1) 1-Kursk State Medical University; 3, K. Marx St., Kursk 305041, Russian Federation 2-Tomsk National Research Polytechnic University; 30, Lenin Pr., Tomsk 634050, Russian Federation

Introduction. 2,6-Di-tert-butylhydroxybenzene (2,6-DTBHB) is a substance that has antioxidant and antiradiation activities and is used as an antioxidant and an intermediate for organic syntheses. The compound is toxic to warm-blooded animals; cases of human poisoning have been recorded. Objective: to investigate the features of determination of 2,6-DTBHB in liver tissues and blood. Material and methods. The investigation object was model mixtures of 2,6-DTBHB and liver tissue. Thin-layer chromatography (TLC), ultraviolet (UV) and infrared (IR) spectrophotometries, and a reaction to obtain an acy-nitro derivative were used for their identification and quantification. Results. The investigation showed how the compound in question could be purified from the endogenous substances of biological matrices by adsorption chromatography in a column packed with silica gel L 40/100 µm, eluting with a mixture of hexane:dioxane (97,5:2,5). Procedures were developed to identify and quantify 2,6-DTBHB in the extracts from biological material, by applying TLC, IR and UV spectrophotometry. The optimal parameters of nitration of 2,6-DTBHB and subsequent transfer of the resultant nitro derivative to stained acy-nitro salt were established. Conclusion. A scheme for examining organ tissues and blood was proposed to confirm that they contain 2,6-DTBHB.

Keywords: 
2
6-Di-tert-butylhydroxybenzene
isolation
chromatographic purification
identification
determination

References: 
  1. 2,6-di-tert-butylphenol. CAS N: 128-39-2. [Electronic resource]. Access mode: http://www.inchem.org/documents/sids/sids/128392.pdf.
  2. Kudryashov Yu.B., Berenfel`d B.S. Osnovy radiacionnoy biofiziki. M.: Izdatel`stvo Moskovskogo universiteta; 1982. [Kudryashov U.B., Berenfeld B.S. Basics of Radiation Biophysics. Moscow: Izdatelstvo Mockovskogo universiteta; 1982 (in Russian)].
  3. Fang Z.-W., Xu D.-Q., Zhang Y.-L., Xiao Y.-R., Zhao J.-F. The Degradation Characteristics of Degrading Bacterium of 2,6-Di-Tert-Butylphenol. Huan Jing Ke Xue, 2004; 25 (3): 98–101.
  4. Ma H., Li G., Zhang Y., Zhang Z., Fang P. Characteristic and Metabolic pathways of 2,6-Di-tert-butylphenol degradation by Alcaligenes F-3-4. Paper presented at: 2011 Second International Conference on Mechanic Automation and Control Engineering; July 15-17, 2011; Inner Mongolia, China. doi: 10.1109/MACE.2011.5987366. Access mode: http://ieeexplore.ieee.org/ document/5987366
  5. Ogata M., Shin-Ya. K., Urano S., Endo T. Antioxidant Activity of Propofol and Related Monomeric and Dimeric. Compounds Chem. Pharm. Bull., 2005; 53(3): 344–6. doi: org/10.1248/cpb.53.344.
  6. Bergel`son M.B., Tatur I.R., Minnebaeva E`.R., Spirkin V.G. Issledovanie fiziko-himicheskih svoystv e`kstraktov selektivnoy ochistki maslyanyh distillyatov i ih smesey s industrial`nymi maslami. Trudy RGU nefti i gaza im. I.M. Gubkina, 2014; (4): 88–98. [Bergelson M.B., Tatur I.R., Minnebaeva E.R., Spirkin V.G. Investigation of the physicochemical properties of the extracts of selective purification of oil distillates and their mixtures with industrial oils. Proceedings of the I.M. Gubkin Russian State University of Petroleum and Gas, 2014; (4): 88–98 (in Russian)].
  7. Milaeva E.R., Gerasimova O.A., Jingwei Z., Shpakovsky D.B et al. Synthesis and antioxidative activity of metalloporphyrins bearing 2,6-di-tert-butylphenol pendants. Journal of Inorganic Biochemistry, 2008;102 (5–6): 1348–58.
  8. Ziakas G.N., Rekka E.A., Gavalas A.M., Eleftheriou P.T., Kourounakis P.N. New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. Bioorg. Med. Chem., 2006;14 (16): 5616–24.
  9. Sentürk M., Gülçin I., Daştan A., Küfrevioğlu O.I., Supuran C.T. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem., 2009;17(8): 3207–11. doi: 10.1016/j.bmc.2009.01.067.
  10. Ruiz J., Pérez C., Pouplana R. QSAR study of dual cyclooxygenase and 5-lipoxygenase inhibitors 2,6-di-tert-butylphenol derivatives. Bioorg Med Chem., 2003; 11(19): 4207–16.
  11. Shormanov V.K., Cacua E.P., Astashkina A.P. Izuchenie sohranyaemosti 2,6-ditretbutilgidroksibenzola v biologicheskom materiale. III Mezhdunarodnaya nauchno-prakticheskaya konferenciya «Osnovnye problemy v sovremennoy medicine»; Oktyabr` 11, 2016. Volgograd. [E`lektronnyy resurs]. Rezhim dostupa: http://izron.ru/conference/med/ [Shormanov V.K., Tcatcua E.P., Astashkina A.P. Study of persistence of 2,6 ditretbutilgidroksibenzola in biological material. III mezdunarodnaya nauchno-prakticheskaya konferenciya «Osnovie problemi v sovremennoi medicine»; Oktyabr` 11, 2016; Volgograd. [Electronic resource]. Access mode: http://izron.ru/conference/med/ (in Russian)].
  12. 128-39-2 (2,6-Di-t-butylphenol). [Electronic resource]. Access mode: https://pubchem.ncbi.nlm.nih.gov/ compound/2_6-di-tert-butylphenol.
  13. Shormanov V.K., Ostanin M.A., Astashkina A.P., Grishechko O.I., Cacua E.P. Osobennosti raspredeleniya 4-metoksigidroksibenzola v organizme teplokrovnyh zhivotnyh (krysy) pri letal`nyh otravleniyah. Sudebno-medicinskaya e`kspertiza, 2016; 59 (4): 48–53. doi: 10.17116/sudmed201659448-53. [Shormanov V.K., Ostanin M.A., Astashkina A.P., Grishechko O.I., Tcatcua E.P. Features of distribution of 4-metoksigidroksibenzola in the body of warm-blooded animals (rats) in fatal poisonings. Sudebno-medicinskaya ekspertiza, 2016; 59 (4): 48–53. doi: 10.17116/sudmed201659448-53 (in Russian)].
  14. James R., Glen J.B. Synthesis, Biological Evaluation, and Preliminary Structure-Activity Considerations of a Series of Alkylphenols as Intravenous Anesthetic Agents. Journal of Medicinal Chemistry, 1980; 23(12):1350–7.
  15. Gandolli C., eds. The dictionary of substances and their effects. Vol. 3. D. Cambridge: Royal Society of Chemistry; 1999.
  16. Shormanov V.K., Cacua E.P., Koropova T.F., Astashkina A.P., Yangolenko G.G. Osobennosti opredeleniya 2-hlor-1,4-digidroksibenzola v biologicheskom materiale. Sudebno-medicinskaya e`kspertiza, 2016; 59 (5): 44–50. doi: 10.17116/sudmed201659544-50. [Shormanov V.K., Tcatcua E.P., Koropova T.F., Astashkina A.P., Yangolenko G.G. Features of the definition of 2-chloro-1,4-dihydroxybenzene in biological material. Sudebno-medicinskaya ekspertiza , 2016; 59 (5):44–50. doi: 10.17116/sudmed201659544-50 (in Russian)].