STUDY OF THE STABILITY OF 2,6-DI-TERT-BUTYL-4-METHYLHYDROXYBENZENE IN BIOLOGICAL MATERIAL

DOI: https://doi.org/10.29296/25877313-2022-01-03
Issue: 
1
Year: 
2022

A.P. Chernova Ph.D. (Chem.), Associate Professor, National Research Tomsk Polytechnic University (Tomsk, Russia) E-mail: apa2004@mail.ru; https://orcid.org/0000-0001-7002-492X M.K. Elizarova Ph.D. (Pharm.), Yeisk Medical College of the Ministry of Health of the Krasnodar Territory (Yeisk, Russia) E-mail: goukkemk@mail.ru; https://orcid.org/0000-0002-8944-4358 V.K. Shormanov Dr.Sc. (Pharm.), Professor, Kursk State Medical University (Kursk, Russia) E-mail: R-WLADIMIR@yandex.ru; https://orcid.org/0000-0001-8872-0691 O.I. Pugacheva Post-graduate Student, Kursk State Medical University (Kursk, Russia) E-mail: lnpugacheva@yandex.ru; https://orcid.org/0000-0002-2074-0423

Aim purpose. Study of stability of 2,6-di-tert-butyl-4-methylhydroxybenzene in biological material. Methods. The studies were carried out by GC-MS, TLC and UV spectrophotometry.2,6-di-tert-butyl-4-methylhydroxybenzene was isolated from the bi-omatrix (liver tissue) by infusion with a mixture of ethyl acetate-acetone (7:3). The analyte was purified by combining extraction (water-ethyl acetate system) and semi-preparative column chromatography (sorbent – silica gel L 40/100 μm, eluent – hexane-acetone (9.5:0.5)), Results. It was found that at –22оС, 2оС, 10оС, 20оС and 30оС. 2,6-di-tert-butyl-4-methylhydroxybenzene remains in the biomaterial for 469, 371, 315, 301 and 259 days, respectively. The possibility of mathematical description of the dynamics of analyte decomposition in biomaterial at the indicated temperatures using the hyperbole equation has been studied. Coefficients in the equation of hyperbola (km), Calculated from the results of the experi-ment, for temperatures of –22оС, 2оС, 10оС, 20оС and 30оС were respectively 11415, 7508, 4983, 3696 and 2156. A linear dependence of km was found. from the storage temperature tо, which is described by the equation: km = 182,24(50–tо) –1702,36. Conclusion. The dynamics of decomposition of 2,6-di-tert-butyl-4-methylhydroxybenzene in the liver tissue at –22оС – + 30оС, which can be de-scribed by the hyperbole equation, is shown. The possibility of predicting the nature of analyte stability in biomaterial in the specified temperature range is shown.

Keywords: 
2
6-di-tert-butyl-4-methylhydroxybenzene
biological material
storability
dynamics of decomposition
prediction of stability

References: 
  1. Butylated hydroxytoluene. PubChem. Open chemistry database. Available at: https://pubchem.ncbi.nlm.nih.gov/com-pound/Butylated-hydroxytoluene. Accessed Ok-tober 26, 2021.
  2. Yehye W.A., Rahman N.A., Ariffin A. et al. Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): A review. European Journal of Medicinal Chemistry. 2015; 101: 295–312. https://doi.org/10.1016/j.ejmech.2015.06.026.
  3. Zhou Z., Wu J., Liu K. et al. Electrochemical Behavior of the Antioxidant 2,6-Di-tert-butyl-4-methylphenol in an Electrolyte Containing Transformer Oils. CSJ Journals. 2017; 46(3): 323–326. https://doi.org/10.1246/cl.161003.
  4. Sun L., Wu C., Xu J. et al. Addition of butylated hydroxytoluene (BHT) in tris-based extender improves post-thaw quality and motion dynamics of dog spermatozoa. Cryobiology. 2020; 97: 71–75. https://doi.org/10.1016/j.cryobiol.2020.10.006.
  5. Merino O., Aguagüiña W.E., Esponda P. et al. Protective effect of butylated hydroxytoluene on sperm function in human spermatozoa cryopreserved by vitrification technique. Andrologia. 2015; 47: 186–193. https://doi.org/10.1111/and.12246.
  6. Wang W., Kannan K. Quantitative identification of and exposure to synthetic phenolic antioxidants, including butylated hydroxytoluene, in urine. Environment inter-national. 2019; 128: 24–29. https://doi.org/10.1016/j.envint.2019.04.028.
  7. Prishchenko A.A., Livantsov M.V., Novikova O.P. et al. Synthesis of organophosphorus derivatives of 2,6-di-tert-butyl-4-methylphenol. Heteroatom Chemistry. 2008; 19(5): 490–494. https://doi.org/10.1002/hc.20458.
  8. Bhardwaj V., Chauhan S., Sharmaa P. Probing effect of lipophilic butylated hydroxytoluene on anionic surfactant properties for potential food and pharmaceutical applications: Thermo-acoustic and spectroscopic study. Fluid Phase Equilibria. 2014; 373: 63–71. https://doi.org/10.1016/j.flu-id.2014.03.032.
  9. Festjens N., Kalai M., Smet J. et al. Butylated hydroxyanisole is more than a reactive oxygen species scavenger. Cell Death Differentiation. 2006; 13: 166–169. https://doi.org/10.1038/sj.cdd.4401746.
  10. Santhakumari S., Jayakumar R., Logalakshmi R. et al. In vitro and in vivo effect of 2,6-Di-tert-butyl-4-methylphenol as an antibiofilm agent against quorum sensing mediated biofilm formation of Vibrio spp. International journal of food microbiology. 2018; 281: 60–71. https://doi.org/10.1016/j.ijfoodmicro.2018.05.024.
  11. Jiang G., Lin S., Wen L. et al. Identification of a novel phenolic compound in litchi (Litchi chinensis Sonn.) pericarp and bioactivity evaluation. Food Chemistry. 2013; 136(2): 563–568. https://doi.org/10.1016/j.foodchem.2012.08.089
  12. Opinion Butylated Hydroxytoluene (BHT). Scientific Committee on Consumer Safety. European Union, 2021. Available at: https://ec.europa.eu/health/sites/default/files/scientific_committees/consumer_safety/docs/sccs_o_257.pdf. Accessed Oktober 26, 2021.
  13. Shormanov V.K., Astashkina A.P., Ostanin M.A. et al. Distribution features of 4-methoxyhydroxybenzene in the body of warm-blooded animals with lethal poisoning. Sudebno-medicinskaya ekspertiza. 2016; 59(4): 48–53.
  14. Shormanov V.K., Pugachyova O.I., Astashkina A.P., Cacua E.P. Distribution features of 2,6-di-tert-butyl-4-methylhydroxybenzene in the body of warm-blooded ani-mals. Sudebno-medicinskaya ekspertiza. 2016; 59(1): 29–34.
  15. Shormanov V.K., Kovalenko E.A., Duricyn E.P. Determination of furadan in biological fluids. Sudebno-medicinskaya ekspertiza. 2005; 48(5): 36–39.