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Chemical Compound Review

Panorama     decan-1-ol

Synonyms: Royaltac, Decanol, Contak, Delete, Antak, ...
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Disease relevance of n-Decyl alcohol

  • Oxygen uptake due to luciferase in two luminous Vibrio species was estimated in vivo by utilizing inhibitors having specificities for luciferase (decanol) and cytochromes (cyanide) [1].
  • In an effort to enhance TPPB activity and applicability, a genetically engineered derivative of Pseudomonas putida ATCC 11172 mutated in its ability to utilize medium-chain-length alcohols was generated (AVP2) and applied as the catalyst within a TPPB system with decanol as the delivery solvent [2].
  • The EASYTRAK was implanted with a pulse generator offering, in addition to resynchronization therapy, either tachycardia monitoring (CONTAK TR) or implantable cardioverter defibrillator therapy (CONTAK CD), depending on the patient indication [3].
  • Glutaconyl-CoA decarboxylase from Acidaminococcus fermentans was inactivated by incubation with n-alkanols at 37 degrees C. The concentration of the alcohol required for complete inactivation decreased with increasing chain length; e.g. 2 M ethanol was as potent as 2 mM hexanol or 0.5 mM decanol [4].
  • The cyclodextrin-glycosyltransferase from Klebsiella pneumoniae M5 al can preferentially be employed at pH 6 to 8, temperatures of 40 to 50 degrees C and a decanol concentration of 0.1 kg-1 starch [5].

Psychiatry related information on n-Decyl alcohol

  • These defense mechanisms allow P. putida DOT-T1E to survive well in the presence of high concentrations of the aliphatic alcohols, and growth with nonanol or decanol occurred at a high rate, whereas in the presence of an octanol double-phase growth was compromised [6].

High impact information on n-Decyl alcohol

  • Contrary to the hypothesis and reported data, we find a strictly linear increase in log(K) as the chain length increases [delta(delta G0)CH2 = - 3.63 kJ/mol] for the primary alcohols from decanol to pentadecanol, with no hint of a cutoff [7].
  • BSA binds the n-alkanols specifically and, at 1 mM total concentration, is stabilized with increasing potency up to decanol (C10), where a loss in stabilizing potency occurs [8].
  • The permeability coefficient increased with increasing lipophilicity to alcohol C8 (octanol) with no further increase for C10 (decanol) [9].
  • For the n-alkanols, butanol to decanol, the concentrations required to reduce the potassium current at 60 mV membrane potential by 50% were determined [10].
  • Decanol was found to be an optimum enhancer among other saturated fatty alcohols that were examined (from octanol to myristyl alcohol) [11].

Biological context of n-Decyl alcohol

  • 3. Increasing the n-alcohol carbon number has been shown to increase the potency of the alcohols up to decanol at concentrations corresponding to EC50s for producing loss of righting reflex in tadpoles [12].
  • Hexanol and decanol also were assayed against freeze-thawed (broken) mitochondria to distinguish effects on the mitochondrial substrate carrier from those on the electron transport chain [13].
  • Effects of a series of n-alcohols (methanol to decanol) were studied on TBPS binding and membrane fluidity (using 1,6-diphenyl-1,3,5-hexatriene as a fluorescent probe) [14].
  • The presence of decanol accelerates the enzymatic hydrolysis of Tos-Ala-OPPy with a kcat/KM = 10(7) M-1 s-1, which is close to the diffusion-controlled limit [15].
  • Evaluation of cation specificity, kinetics of TSQ:Zn binding, quenching of TSQ by dithionite and Zn2+ chelation by D-penicillamine established that TSQ is more fluorescent in decanol or PC vesicles than in aqueous buffer, has a high affinity for lipid bilayers and is specific for Zn2+ compared to Mg2+ and Ca2+ [16].

Anatomical context of n-Decyl alcohol

  • When the effects of heptanol were compared with those of the n-alkanols hexanol and decanol, the efficacies of these agents as suppressors of Con A-stimulated oocyte maturation was directly related to their relative abilities to suppress metabolic coupling.(ABSTRACT TRUNCATED AT 250 WORDS)[17]
  • First, VSV was dispersed in aqueous C(14)AO+ D or DSCG, and then HeLa cells were inoculated by contacting the cells with the aqueous C(14)AO + D or DSCG containing VSV [18].
  • The binding of [3H] concanavalin A as well as its internalization by macrophages incubated with the lectin for 15, 45 and 90 min are not affected significantly in the presence of decanol, procaine or chlorpromazine at concentrations of maximum enhancing effect on vacuolation [19].

Associations of n-Decyl alcohol with other chemical compounds


Gene context of n-Decyl alcohol

  • In a lyotropic nematic matrix of the disk-like N(D) phase in the ternary system hexadecyldimethylethyl ammonium bromide (C16Me2EABr)/water/n-decanol, a disk-like lyotropic cholesteric phase Ch(D) was induced by addition of the axial optically active compound R(-)-1,1'-binaphthalene-2,2'-diyl-hydrogen-phosphate (BDP) [25].
  • 4. In contrast to the lack of behavioural effects by long chain alcohols reported previously, decanol produced loss of righting reflex in short- and long-sleep mice, indicating that the in vivo effects of decanol may be due in part to actions at GABAA receptors [26].
  • We show that we can alter the mechanism of micelle/water partitioning by the addition of decanol as a co-surfactant to an SDS micellar solution [27].
  • The Ventak CHF/CONTAK CD Biventricular Pacing Study is a prospective randomized trial to examine the safety and efficacy of biventricular (BV) pacing in patients with standard indications for an ICD, symptomatic heart failure, a LVEF < or = 0.35, and a QRS > or = 120 ms [28].
  • Experiments indicated that both the formation of decanol and the emulgating effect of the lipase account for these observations [29].

Analytical, diagnostic and therapeutic context of n-Decyl alcohol

  • Cyanide titration of respiration revealed a component of oxygen uptake less sensitive to cyanide which was completely inhibitable by low concentrations of decanol [1].
  • The left ventricular lead was implanted in conjunction with a conventional right ventricular lead and a new heart failure device (CONTAK TR, Guidant, Brussels, Belgium) [3].
  • Potentiometric behavior of ion-selective electrodes to large cationic species modulated by decyl alcohol [30].
  • We report a case of entrainment of sustained monomorphic VT in a 62-year-old female with an ischemic cardiomyopathy and VT, who received a biventricular pacemaker-implantable cardioverter defibrillator, Contak CD (Guidant, St. Paul, MN) [31].
  • In this work, through the Z-scan technique, we report on measurements of the nonlinear refractive index (n_{2}) in discotic and calamitic nematic phases at room temperature in lyotropic mixtures of potassium laurate, decanol and D2O . This technique presents high sensitivity when compared to conventional interferometry [32].


  1. Luciferase-dependent oxygen consumption by bioluminescent vibrios. Makemson, J.C. J. Bacteriol. (1986) [Pubmed]
  2. Enhancement of a two-phase partitioning bioreactor system by modification of the microbial catalyst: demonstration of concept. Vrionis, H.A., Kropinski, A.M., Daugulis, A.J. Biotechnol. Bioeng. (2002) [Pubmed]
  3. Transvenous left ventricular lead implantation with the EASYTRAK lead system: the European experience. Pürerfellner, H., Nesser, H.J., Winter, S., Schwierz, T., Hörnell, H., Maertens, S. Am. J. Cardiol. (2000) [Pubmed]
  4. The sodium pump glutaconyl-CoA decarboxylase from Acidaminococcus fermentans. Specific cleavage by n-alkanols. Buckel, W., Liedtke, H. Eur. J. Biochem. (1986) [Pubmed]
  5. The production of alpha-cyclodextrin by enzymatic degradation of starch. Flaschel, E., Landert, J.P., Spiesser, D., Renken, A. Ann. N. Y. Acad. Sci. (1984) [Pubmed]
  6. Biotransformation in double-phase systems: physiological responses of Pseudomonas putida DOT-T1E to a double phase made of aliphatic alcohols and biosynthesis of substituted catechols. Rojas, A., Duque, E., Schmid, A., Hurtado, A., Ramos, J.L., Segura, A. Appl. Environ. Microbiol. (2004) [Pubmed]
  7. Partitioning of long-chain alcohols into lipid bilayers: implications for mechanisms of general anesthesia. Franks, N.P., Lieb, W.R. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  8. Steric hindrance is not required for n-alkanol cutoff in soluble proteins. Eckenhoff, R.G., Tanner, J.W., Johansson, J.S. Mol. Pharmacol. (1999) [Pubmed]
  9. Determination of the effect of lipophilicity on the in vitro permeability and tissue reservoir characteristics of topically applied solutes in human skin layers. Cross, S.E., Magnusson, B.M., Winckle, G., Anissimov, Y., Roberts, M.S. J. Invest. Dermatol. (2003) [Pubmed]
  10. The actions of some general anaesthetics on the potassium current of the squid giant axon. Haydon, D.A., Urban, B.W. J. Physiol. (Lond.) (1986) [Pubmed]
  11. Microemulsions as transdermal drug delivery vehicles. Kogan, A., Garti, N. Advances in colloid and interface science (2006) [Pubmed]
  12. Enhancement of homomeric glycine receptor function by long-chain alcohols and anaesthetics. Mascia, M.P., Machu, T.K., Harris, R.A. Br. J. Pharmacol. (1996) [Pubmed]
  13. Alkanols inhibit respiration of intact mitochondria and display cutoff similar to that measured in vivo. Hammond, D.G., Kubo, I. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  14. Neurochemical actions of anesthetic drugs on the gamma-aminobutyric acid receptor-chloride channel complex. Huidobro-Toro, J.P., Bleck, V., Allan, A.M., Harris, R.A. J. Pharmacol. Exp. Ther. (1987) [Pubmed]
  15. A kinetic study of the hydrolysis of the N-tosylalanine ester of 3-hydroxy-5-phenylpyrrole and related compounds by human leukocyte elastase. Jackson, D.S., Brown, A.D., Schaeper, R.J., Powers, J.C. Arch. Biochem. Biophys. (1995) [Pubmed]
  16. Characterization of N-(6-methoxy-8-quinolyl)-p-toluenesulfonamide for the detection of zinc in living sperm cells. Andrews, J.C., Nolan, J.P., Hammerstedt, R.H., Bavister, B.D. Cytometry. (1995) [Pubmed]
  17. Metabolic coupling and ligand-stimulated meiotic maturation in the mouse oocyte-cumulus cell complex. Fagbohun, C.F., Downs, S.M. Biol. Reprod. (1991) [Pubmed]
  18. Compatibility of lyotropic liquid crystals with viruses and mammalian cells that support the replication of viruses. Cheng, L.L., Luk, Y.Y., Murphy, C.J., Israel, B.A., Abbott, N.L. Biomaterials (2005) [Pubmed]
  19. Effects of local anaesthetics on intracellular fusion processes. Enhancement of concanavalin A-induced macrophage vacuolation. Raz, A., Goldman, R. Biochim. Biophys. Acta (1976) [Pubmed]
  20. Genetic and developmental factors in the olfactory response of Drosophila melanogaster larvae to alcohols. Cobb, M., Bruneau, S., Jallon, J.M. Proc. Biol. Sci. (1992) [Pubmed]
  21. Cholesterol solubility in organic solvents. Flynn, G.L., Shah, Y., Prakongpan, S., Kwan, K.H., Higuchi, W.I., Hofmann, A.F. Journal of pharmaceutical sciences. (1979) [Pubmed]
  22. Silica particles encapsulated poly(styrene-divinylbenzene) monolithic stationary phases for mu-high performance liquid chromatography. Bakry, R., St??ggl, W.M., Hochleitner, E.O., Stecher, G., Huck, C.W., Bonn, G.K. Journal of chromatography. A. (2006) [Pubmed]
  23. Distribution of macropores in silica particles prepared by using multiple emulsions. Oh, C., Chung, S.C., Shin, S.I., Kim, Y.C., Im, S.S., Oh, S.G. Journal of colloid and interface science. (2002) [Pubmed]
  24. Computer-aided control of water activity for lipase-catalyzed esterification in solvent-free systems. Won, K., Lee, S.B. Biotechnol. Prog. (2001) [Pubmed]
  25. Chirality, twist and structures of micellar lyotropic cholesteric liquid crystals in comparison to the properties of chiralic thermotropic phases. Dörfler, H.D. Advances in colloid and interface science. (2002) [Pubmed]
  26. Actions of long chain alcohols on GABAA and glutamate receptors: relation to in vivo effects. Dildy-Mayfield, J.E., Mihic, S.J., Liu, Y., Deitrich, R.A., Harris, R.A. Br. J. Pharmacol. (1996) [Pubmed]
  27. Linear solvation energy relationships of mixed micelles of sodium dodecyl sulfate and decanol: towards a better model of octanol/water partitioning. Bailey, D.J., Dorsey, J.G. Journal of chromatography. A. (2001) [Pubmed]
  28. Performance of a new steroid-eluting coronary sinus lead designed for left ventricular pacing. Achtelik, M., Bocchiardo, M., Trappe, H.J., Gaita, F., Lozano, I., Niazi, I., Gold, M., Yong, P., Duby, C. Pacing and clinical electrophysiology : PACE. (2000) [Pubmed]
  29. Pseudomonas fluorescens lipase adsorption and the kinetics of hydrolysis in a dynamic emulsion system. Kierkels, J.G., Vleugels, L.F., Geladé, E.T., Vermeulen, D.P., Kamphuis, J., Wandrey, C., van den Tweel, W.J. Enzyme Microb. Technol. (1994) [Pubmed]
  30. Potentiometric behavior of ion-selective electrodes to large cationic species modulated by decyl alcohol. Cabrera, W.J., Kaempfe, M.A., Urzúa, M.D., Ríos, H.E. Journal of colloid and interface science. (2006) [Pubmed]
  31. Entrainment of ventricular tachycardia with a permanent biventricular pacemaker. Luck, J.C., Bhatta, L., Artman, S.E., Wolbrette, D.L., Pantelloni, M.A., Naccarelli, G.V. Journal of interventional cardiac electrophysiology : an international journal of arrhythmias and pacing. (2002) [Pubmed]
  32. Nonlinear refractive index measurements of discotic and calamitic nematic lyotropic phases. Kimura, N.M., Santoro, P.A., Fernandes, P.R., Viscovini, R.C., Gómez, S.L., Palangana, A.J. Physical review. E, Statistical, nonlinear, and soft matter physics (2006) [Pubmed]
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