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Chemical Compound Review

t-Butanol     2-methylpropan-2-ol

Synonyms: Arconol, tBuOH, t-BuOH, tert-Butanol, t-butylalcohol, ...
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Disease relevance of Tertiary-Butyl Alcohol

  • Protective effect of tert-butanol on hyperammonemia [1].
  • Tert-butyl alcohol, an important commodity chemical, additive to unleaded gasoline, and contaminant of drinking water, was evaluated for toxicity and was found to enhance nephropathy in male Fischer 344 rats [2].
  • These reactions involve hydroxyl and alkoxy radicals, as the hemolysis and oxyhemoglobin conversion could be inhibited by t-butanol and butylated hydrotoluene [3].
  • Alternating intraperitoneal injections of metabolically stable tert-butanol and ethanol for 4 consecutive days resulted in a physical dependence on alcohol, which was quantified by the latency and ED50 of picrotoxin-induced CNS hyperexcitability--myoclonic and tonic seizures and mortality--during the withdrawal period [4].
  • When the concentration of t-butanol was increased to 3.5% (v/v), severe toxic reactions were found, that included anorexia, self-mutilation, and deaths from no specific determinable causes [5].

Psychiatry related information on Tertiary-Butyl Alcohol


High impact information on Tertiary-Butyl Alcohol

  • Cell growth and division were inhibited in the presence of n-butanol, whereas sec- and tert-butanol had no such effects [9].
  • The isomers sec- and tert-butanol, which did not activate PLD, did not affect microtubule organization [9].
  • These processes and secretion of granules are suppressed by expression of a catalytically inactive mutant of PLD1 or by the presence of 50 mM 1-butanol but not tert-butanol, an indication that these events are dependent on the catalytic activity of PLD1 [10].
  • Very strong medium effects have been observed when testing the antioxidant activity of dipyridamole (DP) in different media such as benzene, tert-butanol, methanol solutions and egg yolk lecithin unilamellar and multilamellar vesicles [11].
  • When ethanol or t-butanol was added in vitro to membranes labeled with the 5- or 12-doxyl probe, a membrane component of tolerance was revealed; that is, the SPM from ethanol-treated mice required more alcohol to reduce the membrane to a given disordered state [12].

Chemical compound and disease context of Tertiary-Butyl Alcohol


Biological context of Tertiary-Butyl Alcohol


Anatomical context of Tertiary-Butyl Alcohol

  • Our results, in particular, the differential effects of 1-, 2-, and tert-butanol with respect to PA formation and astroglial proliferation, strongly suggest that the antiproliferative effects of ethanol in glial cells are due to the disruption of the PLD signaling pathway [22].
  • It is concluded that t-butyl alcohol exacerbated nephropathy in male Fischer 344 rats and increased renal accumulation of hyaline protein material consistent with alpha-2 mu-globulin deposition [2].
  • Since t-butyl alcohol is not a substrate for alcohol dehydrogenase or catalase, the ability of microsomes to oxidize t-butyl alcohol lends further support for a role for hydroxyl radicals in the microsomal alcohol oxidation system [23].
  • Oxidative demethylation of t-butyl alcohol by rat liver microsomes [24].
  • The efficiency of hydrogen atoms in causing single-strand breaks in double-stranded calf thymus DNA was determined to be 2.3%, while the rate constant for the reaction of tert-butanol radicals with DNA and their efficiency in causing single-strand breaks was determined to be 4.1 x 10(3) dm3 mol-1 s-1 and 2%, respectively [25].

Associations of Tertiary-Butyl Alcohol with other chemical compounds


Gene context of Tertiary-Butyl Alcohol

  • On the other hand, the structurally related tertiary alcohol tert-butanol, which cannot be used by PLD, had no effect on TPA-induced transglutaminase activity [31].
  • The purification procedure of cathepsin S includes acid activation of spleen homogenate, incubation at 37 degrees C, precipitation with (NH4)2SO4 in H2O/tert-butanol medium, gel chromatography, chromatofocusing, covalent chromatography and cation chromatography of FPLC system [32].
  • Previously, we demonstrated that human liver is active in metabolizing MTBE to tert-butyl alcohol (TBA) and that cytochrome P450 (CYP) enzymes play a critical role in the metabolism of MTBE [33].
  • Speculatively, because oxidation of t-butanol to t-butylhydroperoxide results in activation, rather than inhibition, of iNOS and TNF-alpha, the reported ethanol-mediated enhancement of iNOS mRNA may result from the action of the hydroxyethyl radical [34].
  • Organic chemistry on cold molecular films: kinetic stabilization of SN1 and SN2 intermediates in the reactions of ethanol and 2-methylpropan-2-ol with hydrogen bromide [35].

Analytical, diagnostic and therapeutic context of Tertiary-Butyl Alcohol


  1. Protective effect of tert-butanol on hyperammonemia. O'Connor, J.E., Guerri, C., Grisolía, S. N. Engl. J. Med. (1982) [Pubmed]
  2. Retrospective study of possible alpha-2 mu-globulin nephropathy and associated cell proliferation in male Fischer 344 rats dosed with t-butyl alcohol. Takahashi, K., Lindamood, C., Maronpot, R.R. Environ. Health Perspect. (1993) [Pubmed]
  3. Photohemolysis sensitized by the furocoumarin imperatorin and its oxyfunctionalized derivatives. Potapenko AYa, n.u.l.l., Kyagova, A.A., Andina, E.S., Zhuravel, N.N., Lysenko, E.P., Möller, M., Stopper, H., Adam, W., Saha-Möller, C.R. Photochem. Photobiol. (1999) [Pubmed]
  4. Increased sensitivity to picrotoxin as an index of physical dependence on alcohol in the mouse. Szabó, G., Kovács, G.L., Telegdy, G. Drug and alcohol dependence. (1984) [Pubmed]
  5. Development of physical dependence on t-butanol in rats: an examination using schedule-induced drinking. Grant, K.A., Samson, H.H. Pharmacol. Biochem. Behav. (1981) [Pubmed]
  6. Stimulant and depressant properties of sedative-hypnotics in mice selectively bred for differential sensitivity to ethanol. Dudek, B.C., Abbott, M.E., Phillips, T.J. Psychopharmacology (Berl.) (1984) [Pubmed]
  7. Quantitative comparison of maternal ethanol and maternal tertiary butanol diet on postnatal development. Daniel, M.A., Evans, M.A. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
  8. Study of regioselective dialkylation of naphthalene in the presence of reusable zeolite catalysts. Smith, K., Roberts, S.D., el-Hiti, G.A. Org. Biomol. Chem. (2003) [Pubmed]
  9. Phospholipase d activation correlates with microtubule reorganization in living plant cells. Dhonukshe, P., Laxalt, A.M., Goedhart, J., Gadella, T.W., Munnik, T. Plant Cell (2003) [Pubmed]
  10. Phospholipases D1 and D2 regulate different phases of exocytosis in mast cells. Choi, W.S., Kim, Y.M., Combs, C., Frohman, M.A., Beaven, M.A. J. Immunol. (2002) [Pubmed]
  11. Medium effects on the antioxidant activity of dipyridamole. Pedulli, G.F., Lucarini, M., Marchesi, E., Paolucci, F., Roffia, S., Fiorentini, D., Landi, L. Free Radic. Biol. Med. (1999) [Pubmed]
  12. Changes in synaptic membrane order associated with chronic ethanol treatment in mice. Lyon, R.C., Goldstein, D.B. Mol. Pharmacol. (1983) [Pubmed]
  13. Ultrasonic dehalogenation and toxicity reduction of trichlorophenol. Tiehm, A., Neis, U. Ultrasonics sonochemistry. (2005) [Pubmed]
  14. Administration of subtoxic doses of t-butyl alcohol and trichloroacetic acid to male Wistar rats to study the interactive toxicity. Acharya, S., Mehta, K., Rodrigues, S., Pereira, J., Krishnan, S., Rao, C.V. Toxicol. Lett. (1995) [Pubmed]
  15. Production of ascorbyl palmitate by surfactant-coated lipase in organic media. Hsieh, H.J., Nair, G.R., Wu, W.T. J. Agric. Food Chem. (2006) [Pubmed]
  16. Structure studies of amylose-V complexes and retrograded amylose by action of alpha amylases, and a new method for preparing amylodextrins. Jane, J., Robyt, J.F. Carbohydr. Res. (1984) [Pubmed]
  17. Liver lipid disposal following t-butanol administration to rats. Beaugé, F., Clément, M., Nordmann, J., Nordmann, R. Chem. Biol. Interact. (1981) [Pubmed]
  18. The DMAP-catalyzed acetylation of alcohols--a mechanistic study (DMAP = 4-(dimethylamino)pyridine). Xu, S., Held, I., Kempf, B., Mayr, H., Steglich, W., Zipse, H. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  19. Quantitative comparison of physical dependence on tertiary butanol and ethanol in mice: correlation with lipid solubility. McComb, J.A., Goldstein, D.B. J. Pharmacol. Exp. Ther. (1979) [Pubmed]
  20. Chemoselective acylation of fully deprotected hydrazino acetyl peptides. Application to the synthesis of lipopetides. Bonnet, D., Ollivier, N., Gras-Masse, H., Melnyk, O. J. Org. Chem. (2001) [Pubmed]
  21. Biotransformation of 12C- and 2-13C-labeled methyl tert-butyl ether, ethyl tert-butyl ether, and tert-butyl alcohol in rats: identification of metabolites in urine by 13C nuclear magnetic resonance and gas chromatography/mass spectrometry. Bernauer, U., Amberg, A., Scheutzow, D., Dekant, W. Chem. Res. Toxicol. (1998) [Pubmed]
  22. Ethanol inhibits astroglial cell proliferation by disruption of phospholipase D-mediated signaling. Kötter, K., Klein, J. J. Neurochem. (1999) [Pubmed]
  23. Production of formaldehyde and acetone by hydroxyl-radical generating systems during the metabolism of tertiary butyl alcohol. Cederbaum, A.I., Qureshi, A., Cohen, G. Biochem. Pharmacol. (1983) [Pubmed]
  24. Oxidative demethylation of t-butyl alcohol by rat liver microsomes. Cederbaum, A.I., Cohen, G. Biochem. Biophys. Res. Commun. (1980) [Pubmed]
  25. Single-strand breaks in double-stranded DNA irradiated in anoxic solution: contribution of tert-butanol radicals. Udovicić, L., Mark, F., Bothe, E. Radiat. Res. (1996) [Pubmed]
  26. Trace analysis of ethanol, MTBE, and related oxygenate compounds in water using solid-phase microextraction and gas chromatography/mass spectrometry. Cassada, D.A., Zhang, Y., Snow, D.D., Spalding, R.F. Anal. Chem. (2000) [Pubmed]
  27. Electron spin resonance spectroscopy of oxygen radicals generated by synthetic fecapentaene-12 and reduction of fecapentaene mutagenicity to Salmonella typhimurium by hydroxyl radical scavenging. de Kok, T.M., van Maanen, J.M., Lankelma, J., ten Hoor, F., Kleinjans, J.C. Carcinogenesis (1992) [Pubmed]
  28. The effect of free radicals on hepatic 5'-monodeiodination of thyroxine and 3,3',5'-triiodothyronine. Huang, T.S., Boado, R.J., Chopra, I.J., Solomon, D.H., Teco, G.N. Endocrinology (1987) [Pubmed]
  29. Photochemistry of racemic and resolved 2-iodooctane. Effect of solvent polarity and viscosity on the chemistry. Gao, F., Boyles, D., Sullivan, R., Compton, R.N., Pagni, R.M. J. Org. Chem. (2002) [Pubmed]
  30. Catalytic asymmetric dihydroxylation of olefins using a recoverable and reusable OsO(4)2- in ionic liquid [bmim][PF6]. Branco, L.C., Afonso, C.A. Chem. Commun. (Camb.) (2002) [Pubmed]
  31. Phospholipase d signaling and extracellular signal-regulated kinase-1 and -2 phosphorylation (activation) are required for maximal phorbol ester-induced transglutaminase activity, a marker of keratinocyte differentiation. Bollag, W.B., Zhong, X., Dodd, M.E., Hardy, D.M., Zheng, X., Allred, W.T. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
  32. Bovine cathepsins S and L: isolation and amino acid sequences. Dolenc, I., Ritonja, A., Colić, A., Podobnik, M., Ogrinc, T., Turk, V. Biol. Chem. Hoppe-Seyler (1992) [Pubmed]
  33. Metabolism of methyl tert-butyl ether and other gasoline ethers by human liver microsomes and heterologously expressed human cytochromes P450: identification of CYP2A6 as a major catalyst. Hong, J.Y., Wang, Y.Y., Bondoc, F.Y., Lee, M., Yang, C.S., Hu, W.Y., Pan, J. Toxicol. Appl. Pharmacol. (1999) [Pubmed]
  34. Ethanol metabolism is not required for inhibition of LPS-stimulated transcription of inducible nitric oxide synthase. Greenberg, S.S., Xie, J., Ouyang, J., Zhao, X. Alcohol (1999) [Pubmed]
  35. Organic chemistry on cold molecular films: kinetic stabilization of SN1 and SN2 intermediates in the reactions of ethanol and 2-methylpropan-2-ol with hydrogen bromide. Park, S.C., Maeng, K.W., Kang, H. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  36. Effects of some volatile sedative-hypnotics on punished behavior. Witkin, J.M. Psychopharmacology (Berl.) (1984) [Pubmed]
  37. Pulse radiolysis studies indicate that electron transfer is involved in radioprotection by Hoechst 33342 and methylproamine. Martin, R.F., Anderson, R.F. Int. J. Radiat. Oncol. Biol. Phys. (1998) [Pubmed]
  38. Freeze-drying of tert-butyl alcohol/water cosolvent systems: effects of formulation and process variables on residual solvents. Wittaya-Areekul, S., Nail, S.L. Journal of pharmaceutical sciences. (1998) [Pubmed]
  39. A rational approach towards successful crystallization and crystal treatment of human cytomegalovirus protease and its inhibitor complex. Qian, C., Lagacé, L., Massariol, M.J., Chabot, C., Yoakim, C., Déziel, R., Tong, L. Acta Crystallogr. D Biol. Crystallogr. (2000) [Pubmed]
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