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Chemical Compound Review

Hexanols     hexan-1-ol

Synonyms: HEXANOL, Hexalcohol, Amylcarbinol, Caproalcohol, Hydroxyhexane, ...
 
 
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Disease relevance of n-Hexanol

  • In addition to the oxazolidinones, an aminoalcohol derivative, (1RS,2SR)-5-methyl-1-phenyl-2-(3-piperidinopropylamino )hexan-1-ol (MLV-5860) also reduced the rat decerebrate rigidity [1].
  • Regulation of primary alkylsulfatase induction in Pseudomonas C12B: concentration-dependent stimulation-inhibition by exogenous UTP and sodium acetate and inhibition by 1-hexanol [2].
  • The oxidation of n-hexanol via alcohol dehydrogenases, coupled with the generation of ATP by electron transport phosphorylation (ETP), was used as an indicator for energy-toxic effects on the growth of Comamonas testosteroni ATCC 17454 [3].
 

High impact information on n-Hexanol

 

Biological context of n-Hexanol

 

Anatomical context of n-Hexanol

  • A dose of chloramphenicol of 100 mg kg-1 administered i.v. or i.p. results in more than 50% inhibition of 2-hexanol formation catalyzed by microsomes from both organs, but causes no inhibition of 1-hexanol formation [14].
  • Response characteristics of neurones in this first relay station of the olfactory pathway were measured when the antennae were stimulated with five general green leaf volatiles, i.e. cis-3-hexen-1-ol, trans-2-hexenal, cis-3-hexenyl acetate, trans-2-hexen-1-ol and 1-hexanol [15].
  • The structure and molecular packing density of a "mismatched" solute, 1-hexanol, in lipid membranes of dimyristoyl phosphatidylcholine (DMPC) was studied by molecular dynamics simulations [16].
  • Our recent results have shown that cockroach olfactory receptor neurons are able to reliably resolve 10-Hz pulses of the general "green' odorant 1-hexanol, but it is unknown to what extent the central olfactory pathway is able to resolve temporal aspects of a general odor stimulus [17].
  • 4. n-Hexanol at a concentration (5 mM) which causes a fluidization of cell membrane preparations from isolated frog epidermis also increases the sensitivity of Isc to amiloride [18].
 

Associations of n-Hexanol with other chemical compounds

  • In contrast, when conditioned to 1-hexanol, moths failed to distinguish alcohols from ketones of the same chain length [19].
  • New 2-modified 1,3-diacylglycerols such as 1,3-dilauroylglycerol 2-disodiumphosphate and analogues were characterized with respect to their tendency to form reverse micelles in isooctane and isooctane/1-hexanol [20].
  • The encapsulation of cutinase in dioctyl sulfosuccinate reverse micelles establishes a completely new equilibrium characterized by a bimodal population of empty and filled reverse micelles, whose characteristics depend greatly on the interfacial characteristics, that is, on the absence or presence of 1-hexanol [21].
  • Interactions between aroma compounds (d-limonene, ethyl hexanoate, octanal and 1-hexanol) and high amylose cornstarch were studied using inverse gas chromatography [22].
  • An NADP-dependent constitutive alcohol dehydrogenase that can oxidize hexan-1-ol was detected in several Gram-positive and Gram-negative eubacteria and in two yeasts [23].
 

Gene context of n-Hexanol

  • Biooxidation of n-hexanol by alcohol oxidase and catalase in biphasic and micellar systems without solvent [24].
  • Monomeric C18 stationary phases of both high and low bonding density were synthesized and used to correlate selectivity changes caused by stationary phase ordering with those seen by the addition of n-hexanol [25].
  • In contrast, 1-hexanol was formed when exposing cheese to all three wavelengths, resulting in apparent quantum yields of (2-6) x 10(-5) mol x einstein(-1) [26].
  • 1-Hexanol exhibited retention in water with four fractions in the strength order AGP0 > dRG-II > mRG-II > AGP4 but was strongly salted out in the presence of fraction MP0 [27].
  • The system consisted of n-hexanol (0.81%), SDS (3.31%) and n-butanol (6.61%) in 20 mM phosphate buffer, pH 10.0 (89.28%, w/w) [28].
 

Analytical, diagnostic and therapeutic context of n-Hexanol

  • After microwave-solvent extraction (ME) into hexan-1-ol, the samples (0.5-3.0 microliters) of the filtered and extracted solutions were analyzed by gas chromatography [29].
  • Chain-folded lamellar crystals were obtained by isothermal crystallization of dilute n-hexanol or n-octanol solutions [30].
  • Funnel trap field bioassays revealed that green leaf alcohols (i.e. (Z)-3-hexen-1-ol, (E)-2-hexen-1-ol and 1-hexanol) attracted males, whereas the corresponding aldehydes and acetates were behaviourally inactive [31].
  • Third, in titrations with redox inhibitors of the proton pumps, the pattern of the relationship between proton pump conductance and membrane potential was markedly different from protonophoric and non-protonophoric uncouplers: almost linear in the case of DNP, highly non-linear in the case of n-hexane, 1-hexanethiol and 1-hexanol [32].

References

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  2. Regulation of primary alkylsulfatase induction in Pseudomonas C12B: concentration-dependent stimulation-inhibition by exogenous UTP and sodium acetate and inhibition by 1-hexanol. Fitzgerald, J.W., Stewart, G.J., Kight-Olliff, L. Can. J. Microbiol. (1980) [Pubmed]
  3. Energization of Comamonas testosteroni ATCC 17454 for indicating toxic effects of chlorophenoxy herbicides. Loffhagen, N., Härtig, C., Babel, W. Arch. Environ. Contam. Toxicol. (2003) [Pubmed]
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  10. Amination of n-hexanol in supercritical water. Tajima, K., Uchida, M., Minami, K., Osada, M., Sue, K., Nonaka, T., Hattori, H., Arai, K. Environ. Sci. Technol. (2005) [Pubmed]
  11. Comparison between chlorosomes containing bacteriochlorophyll-c and chlorosomes containing bacteriochlorophyll-d isolated from two substrains of green sulfur photosynthetic bacterium Chlorobium vibrioforme NCIB 8327. Saga, Y., Tamiaki, H. J. Photochem. Photobiol. B, Biol. (2004) [Pubmed]
  12. Inverse gas chromatographic method for measurement of interactions between soy protein isolate and selected flavor compounds under controlled relative humidity. Zhou, Q., Cadwallader, K.R. J. Agric. Food Chem. (2004) [Pubmed]
  13. New alpha-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-beta-D-glucopyranosyl diphenylphosphinate. Kadokawa, J., Nagaoka, T., Ebana, J., Tagaya, H., Chiba, K. Carbohydr. Res. (2000) [Pubmed]
  14. Selective inhibition by chloramphenicol of cytochrome P-450 isozymes in rat lung and liver involved in the hydroxylation of n-hexane. Näslund, B.M., Halpert, J. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  15. Integration of olfactory information in the Colorado potato beetle brain. De Jong, R., Visser, J.H. Brain Res. (1988) [Pubmed]
  16. Molecular packing in 1-hexanol-DMPC bilayers studied by molecular dynamics simulation. Pedersen, U.R., Peters, G.H., Westh, P. Biophys. Chem. (2007) [Pubmed]
  17. Responses of cockroach antennal lobe projection neurons to pulsatile olfactory stimuli. Lemon, W.C., Getz, W.M. Ann. N. Y. Acad. Sci. (1998) [Pubmed]
  18. Changes in cell membrane fluidity affect the sodium transport across frog skin and its sensitivity to amiloride. Lagerspetz, K.Y., Laine, A.M. Comparative biochemistry and physiology. A, Comparative physiology. (1987) [Pubmed]
  19. The generalization of an olfactory-based conditioned response reveals unique but overlapping odour representations in the moth Manduca sexta. Daly, K.C., Chandra, S., Durtschi, M.L., Smith, B.H. J. Exp. Biol. (2001) [Pubmed]
  20. 2-modified 1,3-diacylglycerols as new surfactants for the formation of reverse micelles. Frense, D., Haftendorn, R., Ulbrich-Hofmann, R. Chem. Phys. Lipids (1995) [Pubmed]
  21. Cutinase-AOT interactions in reverse micelles: the effect of 1-hexanol. Melo, E.P., Costa, S.M., Cabral, J.M., Fojan, P., Petersen, S.B. Chem. Phys. Lipids (2003) [Pubmed]
  22. Use of inverse gas chromatography to determine thermodynamic parameters of aroma-starch interactions. Boutboul, A., Lenfant, F., Giampaoli, P., Feigenbaum, A., Ducruet, V. Journal of chromatography. A. (2002) [Pubmed]
  23. NADP-dependent alcohol dehydrogenases in bacteria and yeast: purification and partial characterization of the enzymes from Acinetobacter calcoaceticus and Saccharomyces cerevisiae. Wales, M.R., Fewson, C.A. Microbiology (Reading, Engl.) (1994) [Pubmed]
  24. Biooxidation of n-hexanol by alcohol oxidase and catalase in biphasic and micellar systems without solvent. Karra-Chaabouni, M., Pulvin, S., Meziani, A., Thomas, D., Touraud, D., Kunz, W. Biotechnol. Bioeng. (2003) [Pubmed]
  25. Effect of stationary phase solvation on shape selectivity in reversed-phase high-performance liquid chromatography. Cole, S.R., Dorsey, J.G. J. Chromatogr. (1993) [Pubmed]
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  32. The nature of uncoupling by n-hexane, 1-hexanethiol and 1-hexanol in rat liver mitochondria. Canton, M., Gennari, F., Luvisetto, S., Azzone, G.F. Biochim. Biophys. Acta (1996) [Pubmed]
 
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