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Query: CAS:111-87-5 (1-octanol)
 1,465 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

A series of alkyldimethylbenzylammonium chlorides have been synthesized with n-alkyl chain lengths of C1 leads to C18. Octanol/water partition coefficients were determined and the antimicrobial activity assessed as the minimum growth inhibitory concentrations towards twelve strains of micro-organisms, representative of Gram-negative and Gram-positive bacteria, yeasts and fungi. The data were subjected to a numerical analysis. Antimicrobial activity of the compounds was found to be a parabolic function of their lipophilicity and maximized with n-alkyl chain lengths of between C12 and C16. The data fit to quadratic functions estimated for low (C1-C7) and high (C8-C16) alkyl chain length compounds was better than for a single quadratic describing the activity of the complete series (C1-C18). These maximized at log P values corresponding to alkyl-chain lengths of approximately C7 and C14 respectively, and were suggestive of low and high affinity binding sites upon the cell surface. The data analysis allowed the chain lengths of compounds with optimal activity towards the various groups of organisms to be determined. Generally yeasts and fungi were most sensitive towards C12, Gram-positive bacteria towards C14, and the Gram-negative bacteria towards C16. Gram-negative cells were the most resistant towards all the compounds and Gram-positive cells the least.
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PMID:Antimicrobial activity and physico-chemical properties of some alkyldimethylbenzylammonium chlorides. 641 25

Retention times (Rt) for acrylates, methacrylates, and vinyl monomers were measured with two different columns (C18 Corasil and C8 LiChrosorb) using reverse-phase HPLC in order to obtain their partition coefficients between 1-octanol and water (log P). The log P values of test compounds were determined from the regression curves between RT and log P values of a number of standards using C8 LiChrosorb. The log P values obtained in this manner agreed closely with the log P values observed in previous studies. However, the peaks of these compounds were not sharp and some compounds were eluted for more than 10 min. Thus, the measurement of accurate Rt values is tedious. C18 Corasil was therefore used for this experiment in a mobile phase (methanol : water = 85 : 15). The Rt of some methacrylates with P values over 4 were delayed due to the hydrophobic interaction between these compounds and the C18 packing material. However, in the measurable region of the log P values (about -1 to +4), log P correlated linearly with log Rt following two different regression curves: one for aliphatic and aromatic compounds with the functional groups (r = 0.92), and the other for compounds without these groups (r = 0.99). It is concluded that log P values of methacrylates widely used in dentistry can be determined easily and accurately by HPLC.
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PMID:Determination of partition coefficients of acrylates, methacrylates, and vinyl monomers using high performance liquid chromatography (HPLC). 730 62

n-Octanol-Water partition coefficients (K(ow)) were experimentally estimated for: 2,3,7,8-tetrachloro-and 2,3,7,8-tetrabromodibenzo-p-dioxin; 2,3,7,8-tetrachloro-, 2,3,7,8-tetrabromo-, and 1,2,7,8-tetrabromodibenzofuran; 1,2,3,7,8-pentachloro-, 1,2,3,7,8-pentabromo-, 2,3,4,7,8-pentachloro-, and 2,3,4,7,8-pentabromodibenzofuran; 1,2,4,6,8,9-hexachlorodibenzofuran (HxCDF), and 3,4,3',4'-tetrachlorobiphenyl (3,4,3',4'-TCB). The method involved correlation of literature K(ow) with reverse-phase high-performance liquid chromatography (RP-HPLC) retention time for a series of 23 calibration standards and estimation of K(ow) for test compounds from measured RP-HPLC retention. Retention times for all standards and test chemicals were measured in duplicate on the same octadecasilane (C18) reverse-phase column with an isocratic 85:15 methanol:water mobile phase; solutes were detected by uv absorbance (254 nm). Literature log K(ow) values used for the calibration standards had been measured exclusively by the generator column method. Log K(ow) estimates for the test compounds in the present study ranged from 5.45 for 3,4,3',4'-TCB to 6.81 for HxCDF. K(ow) estimates were then plotted against laboratory data for the in vivo 3-day dermal absorption of single equimolar doses (200 pmol and 20 nmol, or approximately 1 nmol/kg and approximately 0.1 mumol/kg) of selected test compounds in male F344 rats. Strong inverse correlations were found between octanol-water partition coefficient estimates and single-dose dermal absorption for most of the compounds studied. In addition, RP-HPLC retention time itself appeared to be as equally suited as K(ow) to such correlations with dermal absorption. The structure-activity relationships suggested in this study were sought in order to explain observed differences in the dermal absorption of polyhalogenated dibenzo-p-dioxin, dibenzofuran, and biphenyl congeners differing in number, position, and/or type (Cl or Br) of halogen substituents. Moreover, these results should be of predictive value in the risk assessment of dermal exposure to polychlorinated dibenzo-p-dioxins, dibenzofurans, biphenyls, and their brominated analogues.
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PMID:Estimation of octanol-water partition coefficients and correlation with dermal absorption for several polyhalogenated aromatic hydrocarbons. 825 87

A series of ara-CDP-rac-1-S-alkyl-2-O-acyl-1-thioglycerols (3-12), analogues of highly active Cytoros2 (1), was prepared, and solubility, lipophilicity, and structure-activity relationships of these conjugates were investigated. The conjugates with sn-1 alkyl (< C18) and sn-2 fatty acyl (< C14) substituents of the thioglycerol were water-soluble, while those with the sn-1 alkyl (> C14) and the sn-2 fatty acyl (> C16) were sparingly soluble. The latter formed micelles upon sonication. Conjugate 7 containing the sn-1 tetradecyl and the sn-2 palmitoyl (C16) groups formed micelles by both sonication and shaking. The partition coefficients (1-octanol/PBS) of the water-soluble conjugates were about 20 times greater than that of ara-C. The water-insoluble showed a more than 40 times increase. A single dose of the micelle-forming conjugates 7 and 10 produced a significant increase in life span (ILS > 421%) with 50% long-term survivors (> 45 days) in mice bearing ip-implanted L1210 lymphoid leukemia. These results were comparable to those of previous micelle-forming conjugate 1 (Cytoros). In contrast, the water-soluble conjugates at single doses were less effective (ILS 81-386% with 0-33% long-term survivors). However, three divided doses of the water-soluble conjugates were found to be as effective as a single dose of micellar solution of the water-insoluble. The results indicate that conjugate 7 and most of the water-soluble derivatives warrant further investigation.
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PMID:Nucleoside conjugates. 13. Synthesis and antitumor activity of 1-beta-D-arabinofuranosylcytosine conjugates of thioether lipids with improved water solubility. 851 Jan 6

The solvent-tolerant bacterium Pseudomonas putida S12, which adapts its membrane lipids to the presence of toxic solvents by a cis to trans isomerization of unsaturated fatty acids, was used to study possible in vivo regiospecificity of the isomerase. Cells were supplemented with linoleic acid (C18:2delta9-cis,delta12-cis), a fatty acid that cannot be synthesized by this bacterium, but which was incorporated into membrane lipids up to an amount of 15% of total fatty acids. After addition of 1-octanol, which was used as an activator of the cis-trans isomerase, the linoleic acid was converted into the delta9-trans,delta12-cis isomer, while the delta9-cis,delta12-trans and delta9-trans,epsilon12-trans isomers were not synthesized. Thus, for the first time, regiospecific in vivo formation of novel, mixed cis/trans isomers of dienoic fatty acid chains was observed. The maximal conversion (27-36% of the chains) was obtained at 0.03-0.04% (v/v) octanol, after 2 h. The observed regiospecificity of the enzyme, which is located in the periplasmic space, could be due to penetration of the enzyme to a specific depth in the membrane as well as to specific molecular recognition of the substrate molecules.
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PMID:Regiospecific effect of 1-octanol on cis-trans isomerization of unsaturated fatty acids in the solvent-tolerant strain Pseudomonas putida S12. 1176 2

The biosynthetic pathway to n-heptane was investigated by examining the effect of the [beta]-keto acyl-acyl carrier protein synthase inhibitor (2R,3S)-2,3-epoxy-4-oxo-7E,10E-dodecadienamide (cerulenin), a thiol reagent ([beta]-mercaptoethanol), and an aldehydetrapping reagent (hydroxylamine) on the biosynthesis of n-[14C]heptane and putative intermediates in xylem sections of Jeffrey pine (Pinus jeffreyi Grev.& Balf.) incubated with [14C]acetate. Cerulenin inhibited C18 fatty acid biosynthesis but had relatively little effect on radiolabel incorporation into C8 fatty acyl groups and n-heptane. [beta]-Mercaptoethanol inhibited n-heptane biosynthesis, with a corresponding accumulation of radiolabel into both octanal and 1-octanol, whereas hydroxylamine inhibited both n-heptane and 1-octanol biosynthesis, with radiolabel accumulation in octyl oximes. [14C]Octanal was converted to both n-heptane and 1-octanol when incubated with xylem sections, whereas [14C]1-octanol was converted to octanal and n-heptane in a hydroxylamine-sensitive reaction. These results suggest a pathway for the biosynthesis of n-heptane whereby acetate is polymerized via a typical fatty acid synthase reaction sequence to yield a C8 thioester, which subsequently undergoes a two-electron reduction to generate a free thiol and octanal, the latter of which alternately undergoes an additional, reversible reduction to form 1-octanol or loss of C1 to generate n-heptane.
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PMID:Evidence for an Elongation/Reduction/C1-Elimination Pathway in the Biosynthesis of n-Heptane in Xylem of Jeffrey Pine. 1222 60

The use of log k derived from reversed phase (RP)-HPLC retention times provides a convenient method for estimating log P(oct) values (P(oct): 1-octanol/water partition coefficient). In order to establish optimal HPLC conditions, the difference between chromatographic (C18 modified column and aqueous methanol eluents) and bulk solvent systems was examined by use of a batch-like equilibration with octane/aqueous methanol. Comparison of values for log P(O/M-W) (log P for the Octane/MeOH-Water partitioning system) and log k measured for monosubstituted pyrazines at different methanol concentrations, showed closest correlation (r, 0.94) with 50% aqueous methanol; and importantly, under these conditions, log k shows even better correlation (r, 0.99) with log P(oct). Effects of residual silanols on HPLC retention with C18 stationary phases were examined. The results show that, in the presence of a small quantity of accessible silanols, the use of 50% aqueous methanol (M50) as eluent yields values of log k directly proportional to log P(oct) in accord with our earlier proposal that use of log k(M50) provides a convenient means for rapid estimation and prediction of log P(oct).
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PMID:Hydrophobicity parameters determined by reversed-phase liquid chromatography. XV: optimal conditions for prediction of log P(oct) by using RP-HPLC procedures. 1249 94

A novel capillary electrophoresis methodology using UV indirect detection (224 nm) for the analysis of trans-fatty acids in hydrogenated oils was proposed. The electrolyte consisted of a pH 7 phosphate buffer at 15 mmol x L(-1) concentration containing 4 mmol.L(-1) sodium dodecylbenzenesulfonate, 10 mmol x L(-1) polyoxyethylene 23 lauryl ether (Brij 35), 2% 1-octanol and 45% acetonitrile. Under the optimized conditions, ten fatty acids, C12:0, C13:0 (internal standard), C14:0, C16:0, C18:0, C18:1c, C18:1t, C18:2cc, C18:2tt and C18:3ccc were baseline-separated in less than 12 min. The proposed methodology was applied to monitor the formation of trans-fatty acids during hydrogenation of Brazilnut oil. A crude oil sample (42.1% linoleic acid, 37.3% oleic acid, 13.4% palmitic acid, and 7.0% stearic acid) was mixed with 0.25% of a nickel-based catalyst and submitted to two independent hydrogenation conditions: 175 degrees C, 3 atm, 545 rpm for 60 min (GH(1) sample), and 150 degrees C, 1 atm, 545 rpm for 30 min (GH(2) sample). For the most severe hydrogenation condition (higher temperature and pressure, under longer reactional period), a more complete conversion of linoleic and oleic acids into stearic acid occurred with concomitant formation of the trans-species, elaidic acid (C18:1t). For the milder hydrogenation procedure that generated sample GH(2), larger amounts of linoleic and oleic acids remained, in addition to the transformations already observed in the GH(1) sample.
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PMID:Method development for the analysis of trans-fatty acids in hydrogenated oils by capillary electrophoresis. 1276 95

The hydrophobicities of dissolved Al, Cu, Mn, and Pb have been determined in various contaminated natural water samples by 1-octanol extraction and C18 column retention. Octanol extraction varied among the metals studied and between the environments sampled but, in general, was greatest for Pb, whose conditional octanol-water partition coefficient, Dow, exceeded unit value in some samples. In most cases, metal partition into octanol either increased with increasing pH or exhibited a maximum under near-neutral conditions. Although the order and pH-dependence of metal retention by the C18 columns was consistent with these observations, the extent of retention was generally greater than the extent of metal extraction by octanol, possibly because of interferences effected by the C18 column matrix. Speciation calculations and results of controlled experiments employing metals in the presence of model ligands suggest that metals may become hydrophobic either by neutralizing relatively hydrophilic ligands or by combining with ligands that are intrinsically hydrophobic themselves. Given that octanol solubility affords an upper estimate of lipophilicity, the results of this investigation may have important implications regarding our understanding of metal bioavailability and toxicity in natural waters.
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PMID:Hydrophobicity and octanol-water partitioning of trace metals in natural waters. 1522 39

In this work, a CE method for the determination of olive oil acidity was proposed. The method was based on an ethanolic extraction (at 60 degrees C) of the oil long-chain free fatty acids (LC-FFAs) components followed by CE determination in pH 6.86 phosphate buffer at 15 mmol/L concentration containing 4 mmol/L sodium dodecylbenzenesulfonate (SDBS), 10 mmol/L polyoxyethylene 23 lauryl ether (Brij 35), 2% v/v 1-octanol and 45% v/v ACN under indirect UV detection at 224 nm. Although this electrolyte promoted baseline separation of myristic acid (C14:0) (internal standard (IS)) and olive oil major components (palmitic acid (C16:0), oleic acid (C18:1c) and linoleic acid (C18:2cc)) in less than 8 min, after a few injections, the electropherogram profiles were severely altered (peak broadening, migration time shifts, etc.) and the current increased substantially. An adsorption study was conducted revealing that the dissolution of the capillary external polyimide coating during the electrophoretic run caused the detrimental effect. After removal of the capillary tip coating, ten consecutive injections could be performed without any disturbances and this simple procedure was, therefore, implemented during quantitative purposes. The reliability of the proposed method was further investigated by the determination of acidity of an extra virgin olive oil sample in comparison to the established methodology (AOCS method Ca 5a-40, alkaline volumetric titration (AVT)). No statistical differences were found within 95% confidence level. A % acidity of 0.39 +/- 0.02 was found for the olive oil sample under consideration.
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PMID:Determination of olive oil acidity by CE. 1794 Nov 22


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