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Chemical Compound Review

n-butanol     butan-1-ol

Synonyms: Butanolo, Hemostyp, Butanolen, butanol, Butalcohol, ...
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Disease relevance of n-butyl alcohol


Psychiatry related information on n-butyl alcohol

  • The acetate and butyrate conversion reactions in vitro were inhibited by physiological levels of acetone and butanol, and this may be another factor in the in vivo regulation of enzyme activity [6].
  • When locomotor activity was the dependent variable, daily n-butanol had no effect [7].
  • Moreover, alpha-(4-fluorophenyl-2-pyrimidinyl)-1-piperazine butanol (BMY 14802), a putative sigma antagonist (1-10 mg/kg i.p.), did not affect CO-induced amnesia, but when simultaneously administered with DTG, it completely prevented its effect in both tests.(ABSTRACT TRUNCATED AT 250 WORDS)[8]
  • Olfaction was assessed using a butanol threshold test, the UPSIT, and a 7-item discrimination test [9].
  • The objective of this study is to assess the use of n-butanol as a suitable odorant for organoleptic training of breath judges [10].

High impact information on n-butyl alcohol


Chemical compound and disease context of n-butyl alcohol


Biological context of n-butyl alcohol


Anatomical context of n-butyl alcohol

  • The release of nascent secretory vesicles from the TGN was sensitive to 1% 1-butanol, a concentration that inhibited PLD-catalyzed formation of phosphatidic acid [23].
  • Within 30 min of adding n-butanol, a potent activator of PLD, cortical microtubules were released from the plasma membrane and partially depolymerized, as visualized with four-dimensional confocal imaging [19].
  • The inhibition was reversed by soluble proteins extracted with butanol from purified membranes or from intact cells [24].
  • Using two enrichment procedures of the (32)P-postlabeling method, nuclease P1 digestion and butanol extraction, we found that all hepatic microsomes were competent to activate 3-NBA [25].
  • The total cellular content of the fluorescent mitochondrial-specific dye rhodamine 123 (Rh-123) was quantified by butanol extraction as a function of time of exposure and dose for a variety of cell lines [26].

Associations of n-butyl alcohol with other chemical compounds

  • Extraction of the purified membrane preparation with 1-butanol yielded an activity in the aqueous phase which resides in a protein probably a glycoprotein, with an estimated molecular weight of 50,000 in solution [27].
  • Both bovine serum albumin and lysozyme partition between water and 1-butanol by the addition of sodium p-toluene sulfonate at pH 2 [28].
  • Downregulation of phosphoinositide production by 1-butanol resulted in diminished PIP(2) in the plasma membrane and eliminated EGF-induced calpain activation [29].
  • In HGF-stimulated hepatocytes, butanol prevented the formation of PA and DG [30].
  • Incubation of extracted tumor cells with crude butanol extracts prepared from those cells restored the cell surface CB-like activity to that of the unextracted controls, suggesting that the increased enzyme activity observed following extraction may be due to the release of an endogenous cysteine protease inhibitor [5].

Gene context of n-butyl alcohol


Analytical, diagnostic and therapeutic context of n-butyl alcohol

  • Moreover, immunization of mice with antigens from the same fractions (fraction II) of n-butanol extracts of C-C26 tumor on the gel filtration could induce the resistance against challenged C-C36 as well as against challenged C-C26 tumor growth [36].
  • Administration of tumor-specific transplantation antigens extracted from viable MCA-F cells with the use of single-phase (2.5%) 1-butanol [crude butanol extract (CBE)] augmented immunity after resection of the primary MCA-F tumor [37].
  • Extraction of a murine tumor-specific transplantation antigen with 1-butanol. I. Partial purification by isoelectric focusing [1].
  • Based upon its ability to inhibit opiate receptor binding, a low-molecular-weight substance (600) has been isolated from human plasma by extraction into butanol and ion exchange, molecular sieve, and thin-layer chromatography [38].
  • C-C26 crude butanol extract was characterized by biochemical procedures including the Sephadex G200 column, lens culinaris affinity column, and anion-exchange Mono Q fast protein liquid chromatography column, and by the enzyme digestion study of the antigens and sodium dodecyl sulfate-polyacrylamide gel electrophoresis [39].


  1. Extraction of a murine tumor-specific transplantation antigen with 1-butanol. I. Partial purification by isoelectric focusing. LeGrue, S.J., Kahan, B.D., Pellis, N.R. J. Natl. Cancer Inst. (1980) [Pubmed]
  2. Differential extraction of tumor-specific transplantation antigen and embryonic antigen from simian virus 40- and adenovirus 7-induced sarcoma cells of hamsters with 1-butanol and 3 M potassium chloride. Coggin, J.H., Gillis, L.D., Payne, W.J. J. Natl. Cancer Inst. (1984) [Pubmed]
  3. Increased brain uptake of gamma-aminobutyric acid in a rabbit model of hepatic encephalopathy. Bassett, M.L., Mullen, K.D., Scholz, B., Fenstermacher, J.D., Jones, E.A. Gastroenterology (1990) [Pubmed]
  4. Differential extraction of tumor-specific antigens from two ultraviolet light-induced murine fibrosarcomas with the use of 1-butanol. Simcik, W.J., Kripke, M.L., Sheu, T.L., LeGrue, S.J. Cancer Res. (1988) [Pubmed]
  5. Identification of cell surface cathepsin B-like activity on murine melanomas and fibrosarcomas: modulation by butanol extraction. Keren, Z., LeGrue, S.J. Cancer Res. (1988) [Pubmed]
  6. Coenzyme A transferase from Clostridium acetobutylicum ATCC 824 and its role in the uptake of acids. Wiesenborn, D.P., Rudolph, F.B., Papoutsakis, E.T. Appl. Environ. Microbiol. (1989) [Pubmed]
  7. 2,4-D-n-butyl ester (2,4-D ester) induced ataxia in rats: role for n-butanol formation. Schulze, G.E. Neurotoxicology and teratology. (1988) [Pubmed]
  8. Behavioral evidence for a modulating role of sigma ligands in memory processes. II. Reversion of carbon monoxide-induced amnesia. Maurice, T., Hiramatsu, M., Kameyama, T., Hasegawa, T., Nabeshima, T. Brain Res. (1994) [Pubmed]
  9. The effect of chronic cocaine abuse on human olfaction. Gordon, A.S., Moran, D.T., Jafek, B.W., Eller, P.M., Strahan, R.C. Arch. Otolaryngol. Head Neck Surg. (1990) [Pubmed]
  10. Use of n-butanol as an odorant to standardize the organoleptic scale of breath odour judges. Saad, S., Greenman, J., Duffield, J., Sudlow, K. Oral diseases. (2005) [Pubmed]
  11. Distribution of butanol molecules along bullfrog olfactory mucosa. Hornung, D.E., Lansing, R.D., Mozell, M.M. Nature (1975) [Pubmed]
  12. Inhibition by alcohols of the localization of radioactive nitrosonornicotine in sites of tumor formation. Waddell, W.J., Marlowe, C. Science (1983) [Pubmed]
  13. Immunologic responsiveness of the C3H/HeJ mouse: differential ability of butanol-extracted lipopolysaccharide (LPS) to evoke LPS-mediated effects. Goodman, M.G., Parks, D.E., Weigle, W.O. J. Exp. Med. (1978) [Pubmed]
  14. Modulation of lipopolysaccharide (LPS)-mediated function by structural differences of two physically distinct fractions of Escherichia coli K235 LPS. Goodman, M.G., Morrison, D.C., Weigle, W.O. J. Immunol. (1977) [Pubmed]
  15. Anti-f Met-Leu-Phe: similarities in fine specificity with the formyl peptide chemotaxis receptor of the neutrophil. Marasco, W.A., Showell, H.J., Freer, R.J., Becker, E.L. J. Immunol. (1982) [Pubmed]
  16. Activators of spleen glucocerebrosidase from controls and patients with various forms of Gaucher's disease. Basu, A., Glew, R.H., Daniels, L.B., Clark, L.S. J. Biol. Chem. (1984) [Pubmed]
  17. C57BL/10/CR mice: nonresponders to activation by the lipid a moiety of bacterial lipopolysaccharide. McAdam, K.P., Ryan, J.L. J. Immunol. (1978) [Pubmed]
  18. Stimulation of respiratory burst by cyclocommunin in rat neutrophils is associated with the increase in cellular Ca2+ and protein kinase C activity. Wang, J.P., Tsao, L.T., Raung, S.L., Lin, P.L., Lin, C.N. Free Radic. Biol. Med. (1999) [Pubmed]
  19. 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]
  20. A 2-O-methylfucose moiety is present in the lipo-oligosaccharide nodulation signal of Bradyrhizobium japonicum. Sanjuan, J., Carlson, R.W., Spaink, H.P., Bhat, U.R., Barbour, W.M., Glushka, J., Stacey, G. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  21. Chemoattractant receptor functions in human polymorphonuclear leukocytes are divergently altered by membrane fluidizers. Yuli, I., Tomonaga, A., Synderman, R. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  22. Antagonists of alcohol inhibition of cell adhesion. Wilkemeyer, M.F., Sebastian, A.B., Smith, S.A., Charness, M.E. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  23. Phospholipase D stimulates release of nascent secretory vesicles from the trans-Golgi network. Chen, Y.G., Siddhanta, A., Austin, C.D., Hammond, S.M., Sung, T.C., Frohman, M.A., Morris, A.J., Shields, D. J. Cell Biol. (1997) [Pubmed]
  24. Reconstitution of membranes and embryonic development in dissociated blastula cells of the sea urchin by reinsertion of aggregation-promoting membrane proteins extracted with butanol. Noll, H., Matranga, V., Cascino, D., Vittorelli, L. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  25. Human enzymes involved in the metabolic activation of the environmental contaminant 3-nitrobenzanthrone: evidence for reductive activation by human NADPH:cytochrome p450 reductase. Arlt, V.M., Stiborova, M., Hewer, A., Schmeiser, H.H., Phillips, D.H. Cancer Res. (2003) [Pubmed]
  26. Increased rhodamine 123 uptake by carcinoma cells. Nadakavukaren, K.K., Nadakavukaren, J.J., Chen, L.B. Cancer Res. (1985) [Pubmed]
  27. Isolation of retina-specific cell-aggregating factor from membranes of embryonic neural retina tissue. Hausman, R.E., Moscona, A.A. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  28. Ligand-promoted transfer of proteins between phases: spontaneous and electrically helped. Mustacich, R.V., Weber, G. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  29. Spatial localization of m-calpain to the plasma membrane by phosphoinositide biphosphate binding during epidermal growth factor receptor-mediated activation. Shao, H., Chou, J., Baty, C.J., Burke, N.A., Watkins, S.C., Stolz, D.B., Wells, A. Mol. Cell. Biol. (2006) [Pubmed]
  30. Phospholipase D activation in hepatocyte growth factor-stimulated rat hepatocytes mediates the expressions of c-jun and c-fos: involvement of protein tyrosine kinase, protein kinase C, and Ca2+. Adachi, T., Nakashima, S., Saji, S., Nakamura, T., Nozawa, Y. Hepatology (1996) [Pubmed]
  31. Differential input by Ste5 scaffold and Msg5 phosphatase route a MAPK cascade to multiple outcomes. Andersson, J., Simpson, D.M., Qi, M., Wang, Y., Elion, E.A. EMBO J. (2004) [Pubmed]
  32. Phospholipase D1 corrects impaired betaAPP trafficking and neurite outgrowth in familial Alzheimer's disease-linked presenilin-1 mutant neurons. Cai, D., Zhong, M., Wang, R., Netzer, W.J., Shields, D., Zheng, H., Sisodia, S.S., Foster, D.A., Gorelick, F.S., Xu, H., Greengard, P. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  33. Mechanism of ADP ribosylation factor-stimulated phosphatidylinositol 4,5-bisphosphate synthesis in HL60 cells. Skippen, A., Jones, D.H., Morgan, C.P., Li, M., Cockcroft, S. J. Biol. Chem. (2002) [Pubmed]
  34. Crosstalk between ARF6 and protein kinase Calpha in Fc(gamma)RI-mediated activation of phospholipase D1. Melendez, A.J., Harnett, M.M., Allen, J.M. Curr. Biol. (2001) [Pubmed]
  35. Inhibition of platelet-derived growth factor-induced cell growth signaling by a short interfering RNA for EWS-Fli1 via down-regulation of phospholipase D2 in Ewing sarcoma cells. Nozawa, S., Ohno, T., Banno, Y., Dohjima, T., Wakahara, K., Fan, D.G., Shimizu, K. J. Biol. Chem. (2005) [Pubmed]
  36. Partial characterization of n-butanol-solubilized rejection-type antigens of syngeneic murine colon tumors. Sato, N., Kikuchi, K. J. Natl. Cancer Inst. (1985) [Pubmed]
  37. Retardation of postsurgical metastases with the use of extracted tumor-specific transplantation antigens and cyclophosphamide. Nomi, S., Pellis, N.R., Kahan, B.D. J. Natl. Cancer Inst. (1984) [Pubmed]
  38. Isolation of a novel endogenous opiate analgesic from human blood. Pert, C.B., Pert, A., Tallman, J.F. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  39. Characterization of tumor rejection antigen molecules of chemically induced murine colon tumor C-C26. Sato, N., Yagihashi, A., Okubo, M., Torigoe, T., Takahashi, S., Sato, T., Kikuchi, K. Cancer Res. (1987) [Pubmed]
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