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Chemical Compound Review

Fuseloel     3-methylbutan-1-ol

Synonyms: Isoamylol, Isopentanol, ISOAMYLALCOHOL, isopentan-1-ol, Fusel Oil, ...
 
 
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Disease relevance of Isopentanol

 

Psychiatry related information on Isopentanol

 

High impact information on Isopentanol

 

Chemical compound and disease context of Isopentanol

 

Biological context of Isopentanol

  • The concept is tested experimentally on a laboratory-scale using, as a model, the esterification of isoamyl alcohol and propionic acid in hexane catalyzed by an immobilized lipase [9].
  • The analysis is made on a porous polymer packing material, by determining the 3-methyl-1-butanol formed on alkaline hydrolysis of the drug [10].
  • The model was validated by using overall uptake data from rodent inhalation studies for three "unreactive" vapors that were either completely inert (i.e., acetone), reversibly ionized in aqueous media (i.e., acrylic acid), or prevented from being metabolized by an enzyme inhibitor (i.e., isoamyl alcohol) [11].
  • At a concentration of 0.5% (v/v), isoamyl alcohol induced the formation of hyphal-like extensions in haploid and diploid strains of Saccharomyces cerevisiae in liquid complex medium [12].
  • To identify genes encoding enzymes with major influence on product formation, a genome-wide gene expression analysis was carried out with S. cerevisiae cells grown at pH 3.0 (optimal for 3-methyl-1-butanol formation) and pH 5.0 (yeast cultivated under standard conditions) [13].
 

Anatomical context of Isopentanol

 

Associations of Isopentanol with other chemical compounds

 

Gene context of Isopentanol

 

Analytical, diagnostic and therapeutic context of Isopentanol

  • Adducts were eluted from the immunoaffinity columns, hydrolyzed with acid, and extracted into isoamyl alcohol, before being subjected to high-performance liquid chromatography [27].
  • With isopentanol alone, the amounts of CYP2H1 and ALAS mRNAs at 4 to 6 h were similar to those observed after treatment with the alcohol combination, but declined by 11 h [28].
  • Total RNA was extracted using proteinase K digestion and phenol/chloroform/isoamyl alcohol extraction, and HCV RNA was detected by standard RT-PCR using primers from the highly conserved 5' untranslated region [29].
  • After isolation by centrifugation, the cpDNA is purified by the combined action of proteolytic enzymes and detergents, followed by the elimination of proteins using a mixture of chloroform and isoamyl alcohol [30].
  • The homogeneity of these two polysaccharides was established by repeated precipitation with iso-amyl alcohol, gel-filtration chromatography and sedimentation analysis [31].

References

  1. Effect of caffeine on acetaminophen hepatotoxicity in cultured hepatocytes treated with ethanol and isopentanol. DiPetrillo, K., Wood, S., Kostrubsky, V., Chatfield, K., Bement, J., Wrighton, S., Jeffery, E., Sinclair, P., Sinclair, J. Toxicol. Appl. Pharmacol. (2002) [Pubmed]
  2. Production of isoamyl acetate in ackA-pta and/or ldh mutants of Escherichia coli with overexpression of yeast ATF2. Vadali, R.V., Horton, C.E., Rudolph, F.B., Bennett, G.N., San, K.Y. Appl. Microbiol. Biotechnol. (2004) [Pubmed]
  3. Pharmacokinetics and pharmacodynamics of ethanol, whiskey, and ethanol with n-propyl, n-butyl, and iso-amyl alcohols. Auty, R.M., Branch, R.A. Clin. Pharmacol. Ther. (1977) [Pubmed]
  4. Characterization of alcohol-induced filamentous growth in Saccharomyces cerevisiae. Lorenz, M.C., Cutler, N.S., Heitman, J. Mol. Biol. Cell (2000) [Pubmed]
  5. A 13C nuclear magnetic resonance investigation of the metabolism of leucine to isoamyl alcohol in Saccharomyces cerevisiae. Dickinson, J.R., Lanterman, M.M., Danner, D.J., Pearson, B.M., Sanz, P., Harrison, S.J., Hewlins, M.J. J. Biol. Chem. (1997) [Pubmed]
  6. In yeast, the pseudohyphal phenotype induced by isoamyl alcohol results from the operation of the morphogenesis checkpoint. Martinez-Anaya, C., Dickinson, J.R., Sudbery, P.E. J. Cell. Sci. (2003) [Pubmed]
  7. Subchronic toxicity studies of 3-methyl-1-butanol and 2-methyl-1-propanol in rats. Schilling, K., Kayser, M., Deckardt, K., Küttler, K., Klimisch, H.J. Human & experimental toxicology. (1997) [Pubmed]
  8. Heterologous expression of the Saccharomyces cerevisiae alcohol acetyltransferase genes in Clostridium acetobutylicum and Escherichia coli for the production of isoamyl acetate. Horton, C.E., Huang, K.X., Bennett, G.N., Rudolph, F.B. J. Ind. Microbiol. Biotechnol. (2003) [Pubmed]
  9. Adsorptive control of water in esterification with immobilized enzymes. Continuous operation in a periodic counter-current reactor. Mensah, P., Carta, G. Biotechnol. Bioeng. (1999) [Pubmed]
  10. Gas-chromatographic determination of camylofine dihydrochloride in tablets and suppositories. Crombez, E., van den Bossche, W., De Moerloose, P. J. Chromatogr. (1976) [Pubmed]
  11. A CFD-PBPK hybrid model for simulating gas and vapor uptake in the rat nose. Bush, M.L., Frederick, C.B., Kimbell, J.S., Ultman, J.S. Toxicol. Appl. Pharmacol. (1998) [Pubmed]
  12. 'Fusel' alcohols induce hyphal-like extensions and pseudohyphal formation in yeasts. Dickinson, J.R. Microbiology (Reading, Engl.) (1996) [Pubmed]
  13. Rapid identification of target genes for 3-methyl-1-butanol production in Saccharomyces cerevisiae. Schoondermark-Stolk, S.A., Jansen, M., Veurink, J.H., Verkleij, A.J., Verrips, C.T., Euverink, G.J., Boonstra, J., Dijkhuizen, L. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  14. Aminopyrine and biphenyl metabolism in cultured hepatocytes. Induction by alcohols. Sinclair, J.F., Wiebkin, P., Zaitlin, L.M., Smith, E.L., Sinclair, P.R. Biochem. Pharmacol. (1984) [Pubmed]
  15. Rapid determination of methadone in plasma, cerebrospinal fluid, and urine by gas chromatography and its application to routine drug monitoring. Schmidt, N., Sittl, R., Brune, K., Geisslinger, G. Pharm. Res. (1993) [Pubmed]
  16. Synergistic induction of cytochrome P450 by ethanol and isopentanol in cultures of chick embryo and rat hepatocytes. Louis, C.A., Sinclair, J.F., Wood, S.G., Lambrecht, L.K., Sinclair, P.R., Smith, E.L. Toxicol. Appl. Pharmacol. (1993) [Pubmed]
  17. Evaluation of a procedure for the simultaneous determination of oxidized and reduced pyridine nucleotides and adenylates in organic phenol extracts from mitochondria. Noack, H., Kunz, W.S., Augustin, W. Anal. Biochem. (1992) [Pubmed]
  18. Cell extensions in PKC1 mutants of Saccharomyces cerevisiae. Azuma, M., Torii, S., Kato, J., Ooshima, H. Can. J. Microbiol. (1999) [Pubmed]
  19. Liquid-chromatographic procedure for tricyclic drugs and their metabolites in plasma. Vandemark, F.L., Adams, R.F., Schmidt, G.J. Clin. Chem. (1978) [Pubmed]
  20. Development of a sensitive radioassay of histamine for in vitro allergy testing. Faraj, B.A., Gottlieb, G.R., Camp, V.M., Kutner, M., Lolies, P. J. Nucl. Med. (1984) [Pubmed]
  21. Involvement of Toll-like receptor 4 in acetaminophen hepatotoxicity. Yohe, H.C., O'Hara, K.A., Hunt, J.A., Kitzmiller, T.J., Wood, S.G., Bement, J.L., Bement, W.J., Szakacs, J.G., Wrighton, S.A., Jacobs, J.M., Kostrubsky, V., Sinclair, P.R., Sinclair, J.F. Am. J. Physiol. Gastrointest. Liver Physiol. (2006) [Pubmed]
  22. Balance of activities of alcohol acetyltransferase and esterase in Saccharomyces cerevisiae is important for production of isoamyl acetate. Fukuda, K., Yamamoto, N., Kiyokawa, Y., Yanagiuchi, T., Wakai, Y., Kitamoto, K., Inoue, Y., Kimura, A. Appl. Environ. Microbiol. (1998) [Pubmed]
  23. Should a lower treatment line be used when treating paracetamol poisoning in patients with chronic alcoholism?: a case for. Buckley, N.A., Srinivasan, J. Drug safety : an international journal of medical toxicology and drug experience. (2002) [Pubmed]
  24. Ethanol and isopentanol increase CYP3A and CYP2E in primary cultures of human hepatocytes. Kostrubsky, V.E., Strom, S.C., Wood, S.G., Wrighton, S.A., Sinclair, P.R., Sinclair, J.F. Arch. Biochem. Biophys. (1995) [Pubmed]
  25. Isolation and characterization of the ATF2 gene encoding alcohol acetyltransferase II in the bottom fermenting yeast Saccharomyces pastorianus. Yoshimoto, H., Fujiwara, D., Momma, T., Tanaka, K., Sone, H., Nagasawa, N., Tamai, Y. Yeast (1999) [Pubmed]
  26. Pyruvate decarboxylase encoded by the PDC1 gene contributes, at least partially, to the decarboxylation of alpha-ketoisocaproate for isoamyl alcohol formation in Saccharomyces cerevisiae. Yoshimoto, H., Fukushige, T., Yonezawa, T., Sakai, Y., Okawa, K., Iwamatsu, A., Sone, H., Tamai, Y. J. Biosci. Bioeng. (2001) [Pubmed]
  27. Derivative fluorescence spectral analysis of polycyclic aromatic hydrocarbon-DNA adducts in human placenta. Weston, A., Manchester, D.K., Poirier, M.C., Choi, J.S., Trivers, G.E., Mann, D.L., Harris, C.C. Chem. Res. Toxicol. (1989) [Pubmed]
  28. Mechanism of the synergistic induction of CYP2H by isopentanol plus ethanol: comparison to glutethimide and relation to induction of 5-aminolevulinate synthase. Louis, C.A., Wood, S.G., Walton, H.S., Sinclair, P.R., Sinclair, J.F. Arch. Biochem. Biophys. (1998) [Pubmed]
  29. Detection of hepatitis C viral sequences in formalin-fixed, paraffin-embedded liver tissue: effect of interferon alpha therapy. Diamond, D.A., Davis, G.L., Qian, K.P., Lau, J.Y. J. Med. Virol. (1994) [Pubmed]
  30. Chloroplast DNA extraction from herbaceous and woody plants for direct restriction fragment length polymorphism analysis. Mariac, C., Trouslot, P., Poteaux, C., Bezançon, G., Renno, J.F. BioTechniques (2000) [Pubmed]
  31. Characterization of EDTA-soluble polysaccharides from the scape of Musa paradisiaca (banana). Raju, T.S., Jagadish, R.L., Anjaneyalu, Y.V. Biotechnol. Appl. Biochem. (2001) [Pubmed]
 
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