Fatty Alcohols

Project ID

2760

Category

OPPT

Added on

Oct. 23, 2018, 8:28 a.m.

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Journal Article

Abstract  The essential oils of two species of Sideritis growing spontaneously in Bulgaria and Macedonia are reported, Sideritis scardica and Sideritis raeseri. The oils of S. scardica from different locations differed significantly: in the Macedonian sample alpha-cadinol (20%) predominated, while in the oil of Bulgarian samples the main components were diterpenic compounds and octadecenol (over 20%). This is the first report of ditrpenoids in essential oil of S. scardica. The oil of S. raeseri demonstrated a distinct chemical profile with its high concentration of sesquiterpenes, main components being germacrone (25%) and elemol acetate (15.9%). The observed qualitative variability of the oil composition of S. scardica of different geographic origin could be a result of different ecologic conditions but might also reflect the well-known tendency of some Sideritis species to hybridize.

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Journal Article

Abstract  Extractive citric acid fermentation with Aspergillus niger microoganism was investigated in the presence of corn oil and Hostarex A327 in oleyl alcohol. In the extractive fermentation, production and separation phases are achieved simultaneously. Before Response Surface Methodology (RSM) was applied,the effect of potassium ferrocyanide (K4Fe(CN)(6)) concentration on citric acid production and the prevention of solvent toxicity using corn oil were investigated. Citric acid concentration increased with increasing K4Fe(CN)(6) concentration. Solvent toxicity was reduced using corn oil in the extractive citric fermentation, In the RSM, the potassium ferrocyanide concentration, (0.02-0.10%, w/v), the ratio of organic phase volume to the aqueous phase volume, V-or/V-aq, (0.5-1.5), the corn oil concentration (0-20%, by volume) and the Hostarex A327 content in oleyl alcohol (10-50% by volume) were the critical components. Optimum citric acid concentration was obtained as 5.70 g/l with employing the following predicted optimum extraction conditions: K4Fe(CN)(6) of 0.06% (w/v), V-or/V-aq of 1.25. corn oil concentration of 13.7% (by volume) and Hostarex A327 content in oleyl alcohol of 33% (by volume). Citric acid production by extractive fermentation was increased approximately 40% with respect to the control run (4.10 g/l). (C) 2002 Elsevier Science Ltd. All rights reserved.

Journal Article

Abstract  We analyzed a single nucleotide polymorphism (SNP) at position -56 (T-->C) in the promoter region of the gene encoding the human interferon-gamma receptor ligand-binding chain I (IFN-gammaR1). The mutation was present at similar frequencies in Gabonese children with either mild or severe malaria. Functional investigations of the promoter in a transfected human B-cell line showed lower levels of luciferase reporter gene expression in the presence of the mutation, indicating the importance of this position for promoter activity, and suggesting that this SNP might negatively influence the expression level of IFN-gammaR1 at the cell surface. Further examinations of the DNA sequence at this polymorphic site showed a perfectly matched binding site for the transcription factor activator protein 4 (AP-4) on both strands. Binding sites for other important transcription factors involved in gene expression and regulation of the immune response against infections, including Ikaros 2 (Ik-2), nuclear factor kappaB (NFkappaB), and CETS1p54, are also situated in this region.

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Journal Article

Abstract  The CTP:phosphocholine cytidylyltransferase (CT) gene from yeast and cDNA from rat liver were over-expressed 20-30-fold in COS cells. Most of the CT activities were found in the cytosolic fraction. The regulation of the yeast CT activity (Y-CT) by lipids was characterized for the first time in comparison with the regulation of the well-studied rat CT (R-CT). Sonicated vesicles composed of egg phosphatidylcholine (PC) or 1-stearoyl-2-oleoyl PC had no effect on Y-CT and only slightly stimulated R-CT activity. Both CTs were activated 10-50-fold by the anionic lipids cardiolipin, phosphatidylglycerol, phosphatidylinositol and oleic acid. The effects of varying the vesicle concentration and the mol% of anionic lipid in PC vesicles were tested. The concentration optima for the activation of Y-CT by oleic acid or anionic phospholipids were 5-10-fold lower than those for R-CT. For example, the stimulation of Y-CT activity by phosphatidylglycerol vesicles was optimal between 5 and 15-mu-m and declined at higher concentrations, but R-CT activation by these vesicles saturated at approximately 25 pm. The positively charged aminolipid sphingosine antagonized the stimulation by oleic acid of both Y-CT and R-CT. Y-CT activity was insensitive to PC vesicles containing the neutral lipids diacylglycerol, monoacylglycerol or oleyl alcohol. However, R-CT was stimulated 10-20-fold by vesicles containing these neutral lipids. Translocation of the CTs to microsomal membranes enriched with anionic or neutral lipids was compared. Oleic acid enrichment promoted translocation of Y-CT and R-CT, whereas diacylglycerol promoted only R-CT translocation. These data show that the activity of Y-CT is lipid-sensitive. Y-CT is affected only by charged lipids, whereas R-CT responds to charged and neutral lipid activators. The data are consistent with different modes of interaction of the two CTs with lipids.

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Journal Article

Abstract  Stearyl and cetyl alcohols are the least irritating of the alcohols, and are present in many topical medicaments as vehicle ingredients. The commercial stearyl and cetyl alcohols used are not pure, but contain impurities, including other alcohols that may be potent sensitizers. We report here a case of contact dermititis due to impurities in stearyl and cetyl alcohols.

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Journal Article

Abstract  The object of this study was to prepare rosiglitazone maleate (RM) sustained-release floating microspheres and investigate their pharmacokinetics. AM microspheres were prepared with ethyl cellulose (EC) and octadecyl alcohol as the carrier materials by an emulsion-solvent diffusion method, and the properties of morphology in vitro floating capability, drug loading (DL), entrapment efficiency (EE), in vitro release and in vivo pharmacokinetics were investigated. The prepared microspheres had a completely spherical shape. The percentage of microspheres floating after 12h was (91.45 +/- 1.62)%, and the DL and EE were (9.31 +/- 0.31)% and (89.55 +/- 1.65)% respectively. Pharmacokinetic studies demonstrated that the RM floating microspheres were superior to commercial tablets in terms of the decrease in peak plasma concentration and maintenance of AM concentration in plasma. The area under the curve of plasma concentration time (AUC) of the floating microspheres was equivalent to that of reference tablets. The results showed that floating microspheres are a feasible approach for the sustained-release preparation of drugs which have limited absorption sites in the upper small intestine.

Journal Article

Abstract  Stearyl heptanoate is an ester of stearyl alcohol and heptanoic acid that functions in cosmetics as a skin conditioning agent and is in the general class of chemicals called stearyl alkanoates. Stearyl caprylate, stearyl palmitate, stearyl stearate, stearyl behenate, and stearyl olivate are stearyl alkanoates with similar chemical structures, toxicokinetics, and functions in cosmetics. These water-insoluble stearyl alkanoates, when metabolized, yield stearyl alcohol and a corresponding fatty acid. The available information supports the safety of all of the related stearyl alkanoates. The Expert Panel concluded that stearyl heptanoate, stearyl caprylate, stearyl palmitate, stearyl stearate, stearyl behenate, and stearyl olivate are safe in the present practices of use and concentration.

Journal Article

Abstract  Two sex pheromone components of the gum leaf skeletonizer, Uraba lugens (Lepidoptera: Nolidae), recently established in New Zealand, were identified. Gas chromatography (GC) electroantennographic detection analyses of female pheromone gland extracts gave three compounds that consistently elicited antennal responses. Chemical analyses, using GC and GC-mass spectrometry, in conjunction with 4-methyl-1,2,4-triazoline-3,5-dione and dimethyldisulfide derivatizations, identified these compounds as (10E,12Z)-hexadecadien-1-yl acetate (E10,Z12-16:Ac), (10E,12Z)-hexadecadien-1-ol (E10,Z12-16:OH), and (Z)-11-hexadecen-1-yl acetate (Z11-16:Ac). A trapping trial in Queensland, Australia, in 2002, indicated that a blend of the two major components E10,Z12-16:Ac and E10,Z12-16:OH could attract gum leaf skeletonizer males. In the same trial, E10,Z12-16:Ac alone trapped large numbers of an unidentified nolid, Nola spp. Further trials in Auckland, New Zealand established that these two components were sufficient and necessary for trap catch of males; adding minor gland components, (10E,12E)-hexadecadien-1-yl acetate (E10,E12-16:Ac), Z11-16:Ac, or octadecan-1-ol (18:OH), to the two-component lure did not result in increased trap catches. Behavioral observations and gland analyses of the Auckland population revealed that female moths begin calling soon after emergence, with peak calling and pheromone production occurring 7 hr into the scotophase. Analysis of gland extract at two-hourly intervals during the first activity period showed that the ratio of E10,Z12-16:Ac to E10,Z12-16:OH (mean of 86: 14, respectively) and pheromone titer were fairly constant. No qualitative or quantitative differences in pheromone components were detected between gland extracts from Tasmanian univoltine and Auckland bivoltine populations of U. lugens.

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Journal Article

Abstract  Immobilized Clostridium acetobutylicum was used to ferment glucose into acetone and butanol in a fluidized-bed bioreactor. A nontoxic immiscible solvent, oleyl alcohol, was added to, and removed directly from, the fermenting columnar reactor and extracted the majority of the inhibitory butanol from the aqueous broth. The extracting solvent had a distribution coefficient of near 3 for butanol. Nonfermenting system tests indicated that equilibrium between the phases could be reached in one pass through the column. Steady-state results are presented for the fermentation with and without the extractive solvent addition. One run, with a continuous aqueous feedstream containing 40 g/L glucose, was operated for 23 d. A steady state was established with just the aqueous feedstream. Approximately half of the glucose was consumed, and the pH fell to 4.5 from 6.5. Then, during multiple intervals, the flow of organic extractive solvent (oleyl alcohol) was begun into the fermenting columnar reactor. A new apparent steady state was reached in about 4 h. The final aqueous butanol concentration was lowered by more than half. The total butanol production rate increased by 50-90% during the solvent extraction, as the organic-to-aqueous ratio increased from 1 to 4, respectively. There was an observed maximum volumetric productivity of 1.8 g butanol h-1L-1 in this nonoptimized system. The butanol yield apparently improved because of the removal of the inhibition. More substrate is going to the desired product, butanol, and less to maintenance or acid production, resulting in 10-20% increases in the ratio of butanol relative to all products.

Journal Article

Abstract  PURPOSE: We examined the available data from clinical trials for certain botanicals used for lower urinary tract symptoms secondary to benign prostatic hyperplasia, including Serenoa repens (saw palmetto), Pygeum africanum (African plum), Secale cereale (rye pollen) and Hypoxis rooperi (South African star grass).

MATERIALS AND METHODS: MEDLINE and The Cochrane Library searches were done in June 2007 using the terms benign prostatic hyperplasia, lower urinary tract symptoms, phytotherapy, saw palmetto, Serenoa, Permixon, Pygeum africanum, Tadenan, Cernilton, Cernitin and Hypoxis. Search results were assessed for relevance and the inclusion of placebo controlled trials.

RESULTS: Two systematic reviews and 3 clinical trials were examined in the evaluation of Serenoa repens. Data from the systematic reviews showed an improvement in flow rates and symptoms. The results of 1 clinical trial were equivocal and the remaining 2 trials clearly showed equivalence to placebo. Systematic reviews were used in the evaluation of P. africanum, Secale cereale and Hypoxis rooperi. P. africanum and H. rooperi showed an improvement in flow rates and symptoms compared to placebo, while S. cereale showed an improvement in symptoms but not flow rates compared to placebo.

CONCLUSIONS: Most clinical trials of investigating the efficacy of botanicals suffer from well documented methodological flaws. Saw palmetto has been clearly shown as comparable to placebo in a trial of sound methodology. While preliminary results appear promising, to our knowledge the remaining botanicals have yet to be evaluated in a trial of similar quality.

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Journal Article

Abstract  As long-chain alcohol dehydrogenases are not easily available and seldom reported enzymes, it is worthwhile to appraise the potential of well known dehydrogenases, like horse liver alcohol dehydrogenases (HLAD), for the oxidation of long-chain aliphatic alcohols. Oxidation of docosanol (C-22) and tetracosanol (C-24) is of technological relevance within an industrial platform for the fractionation and upgrading of tall-oil from the Kraft pulping process. Results are presented on the characterization of free and immobilized HLAD with respect to their potential for oxidizing long-chain aliphatic alcohols. Enzyme activity with respect to chain length and pH is presented. Activity for both free and immobilized HLAD increased with pH up to 8.8, but behavior with respect to chain length varied from one biocatalyst to the other. Even though both biocatalysts were less active towards very long-chain aliphatic alcohols, immobilized HLAD had an activity on docosanol and tetracosanol higher than 50% of the value obtained with ethanol, butanol and octanol, which is encouraging and has not been previously reported. Investigation on thermophilic sources and further immobilization strategies are underway to obtain more active and stable catalysts amenable for working at high temperatures which is quite relevant in this case due to the poor solubility of substrates. (C) 2008 Elsevier Inc. All rights reserved.

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Journal Article

Abstract  A modified USP paddle method using minibaskets was used to study the effects of various formulations on in vitro dissolution of ibuprofen microspheres. Formulations containing waxes such as paraffin or ceresine wax without modifiers exhibited very slow dissolution profiles and incomplete release, which did not improve with increased drug loading or the preparation of smaller microspheres. The addition of modifiers such as stearyl alcohol and glyceryl monostearate greatly increased the dissolution rate, with 20% (w/w) near the optimum for predictable dissolution. Higher drug loading and decreased microsphere size increased the dissolution rate from microspheres containing modifier. Optimum formulations contained ceresine wax or microcrystalline wax and stearyl alcohol as a modifier, with a drug content of 17%. An increase in the encapsulation dispersant concentration had little effect on the dissolution profiles. The dissolution data from narrow size fractions of microspheres indicated spherical matrix drug release kinetics; the 50% dissolution time decreased with the square of the microsphere diameter. With appropriate modifiers, wax microsphere formulations of drugs with solubility characteristics similar to those of ibuprofen can offer a starting basis for predictable sustained release dosage forms.

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Journal Article

Abstract  The dilational viscoelasticity properties of decane-water interface containing two demulsifiers with straight chain SP169 (octadecanol polyoxypropylene-polyoxyethylene ether) and branch chain AE121 (tetraethylenehexamine polyoxypropylene-polyoxyethylene ether) respectively were investigated. The dependence of dilational modulus on dilational frequency and demulsifier concentration was expounded. The influences of two demulsifiers on dilational properties of oil-water interface containing surface-active fraction from crude oil were also studied. The dynamic interfacial tensions between solutions of two demulsifiers and decane were measured and were related to the interfacial dilational rheology properties. The results showed that the two demulsifiers could decrease remarkbly the dilational modulus of oil-water interface containing surface-active fraction from crude oil. At low concentration, because of stronger adsorption ability, the effect of decreasing dilational modulus of SP169 was better. But above a certain concentration, AE121 was preferential because of its higher substitution ability. Since the interface film containing demulsifier had a certain dilational modulus itself, the dosage of demulsifier could not be much higher.

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Journal Article

Abstract  We demonstrate the existence of an anomalous, strong attraction between small (9 nm) oleic acid-grafted magnetite particles and octadecanol-grafted silica spheres (420 nm) in apolar solvents. This attraction manifests itself by irreversible adsorption of magnetite particles onto silica spheres, with surface coverages up to 30%. This "heteroflocculation" is, quite surprisingly, orders of magnitude slower than a diffusion-limited process. The adsorption can be reversed by transferring covered silica particles to solvents with a higher dielectric constant. The findings practically rule out van der Waals forces or Coulomb forces between any pre-existing surface charges as the source of attraction.

WoS
Journal Article

Abstract  The study represents the first part of a series of papers on physico-chemical measurements carried out by gas chromatography. The distribution constant, the liquid film surface areas, the retention volumes corrected for the adsorption at interface, and the quadratic equation that describes the temperature dependence on retention volume for solutes in n-octadecanol as stationary phase at 65-90 degrees C are presented.

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Journal Article

Abstract  Monolayers of straight chain and 2-methyl branched chain alcohols with alkyl chain lengths of C-10-C-18 are experimentally studied by a conventional film balance technique combined with a Brewster angle microscope (BAM). The comparison of the surface pressure (pi)-area (A) isotherms with the corresponding BAM images provides information on the phase behavior and the first-order main phase transition of the monolayers. Striking differences in the dependence of the phase transition pressure on temperature of the straight chain and 2-methyl-substituted alcohols are correlated with differences in the molecular ordering. The general conditions for the main phase transition in the corresponding homologous alcohols can be derived. The effect of alkyl chain length and 2-methyl substitution on the general textural features of the condensed phase domains is determined under equilibrium and nonequilibrium conditions. n-Alcohol monolayers form defined and well-shaped condensed phase domains, often with inner texture in equilibrium. The long-range orientational order is strongly reduced in the condensed phase of 2-methyl-alcohols. Therefore, in the two-phase coexistence region of 2-methyl-alcohol monolayers only irregularly shaped domains without any inner structure are formed, which cannot be observed at the medium alkyl chain length C-14 because of the low contrast. Model calculations of the two-dimensional lattice structure of the racemic 2-methyl-hexadecanol on the basis of the pg space group are performed and correspond well with the reduced ordering concluded from the experiments.

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Journal Article

Abstract  Stable dispersions of monodisperse colloidal silica spheres containing a dye or fluorophore have been synthesized according to a general procedure and dispersed in polar and apolar liquids. The procedure consists of the coupling of the dye to a silane coupling agent, (3-aminopropyl)triethoxysilane, and the controllable incorporation of the reaction product into the silica sphere. The silica spheres are prepared from tetraethoxysilane in mixtures of ammonia, water, and ethanol. The composition of the silica spheres can be controlled in such a way that the organic groups can be placed on the surface, in a thin shell inside the particle or distributed through the volume of an inner core. Fluorescein isothiocyanate was used to make easily bleachable, fluorescent silica spheres. Hydrophilic charge stabilized and organophilic sterically stabilized 1-octadecanol-coated dyed silica systems were synthesized and dispersed in several solvents. All the particles were characterized after the several reaction steps by static and dynamic light scattering and transmission electron microscopy. The fluorescent spheres were further characterized by fluorescence spectroscopy and confocal scanning laser fluorescence microscopy. Great effort was taken to prepare monodisperse dispersions free of clusters of particles. Such model dispersions are required for (scattering) studies of interparticle interactions in (concentrated) systems. Therefore, the several steps of the synthesis and optical characterization are described in detail.

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Journal Article

Abstract  A PVP/SA adduct was prepared by reacting of N-vinylpyrrolidone with stearyl alcohol in presence of ammonium persulphate as initiator in different preparation reaction conditions. The optimum conditions to prepare that adduct are VP/SA, 25%; LR, 1 I/kg; reaction temperature, 80 degrees C and reaction time, 40 min. The graft copolymerization of N-vinylpyrrolidone onto stearyl alcohol was confirmed by the FTIR analysis. The TEM image of the prepared adduct emulsion shows that its particle size ranges from 45 to 173 nm. Finishing of cotton/polyester fabric sample with easy care finishing bath containing 80 g/l of that adduct emulsion results in an increasing in the tensile strength, water repellency rating, antibacterial properties, softness degree, and stiffness along with a reduction in the resiliency of treated fabric. The surface of the prepared adduct treated fabric was characterized via scanning electron microscope. (C) 2017 Elsevier B.V. All rights reserved.

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Journal Article

Abstract  Condensed monolayers of octadecanol have been formed on the surface of single water drops suspended in ambient air by acoustic levitation. As known from former work which has been mostly carried out on Langmuir troughs many monolayers are able to reduce remarkably the evaporation rate at the air-water interface. In contrast to Langmuir troughs, acoustic levitation offers the advantages of a minimized and contact-less technique. The surface area of an evaporating water drop suspended in ambient air declines linearly with time described by the evaporation constant K. After adding octadecanol a condensed monolayer is formed on the drop surface while the drop evaporates. During this process, the evaporation constant is scaled down by a factor of approximately 20. (c) 2007 Elsevier B.V. All rights reserved.

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Journal Article

Abstract  In this Technical Note, the use of a liquid metal, i.e., a low melting point Pb-Sn-In-Bi alloy, as the phase change material (PCM) in thermal energy storage-based heat sinks is tested in comparison to an organic PCM (1-octadecanol) having a similar melting point of similar to 60 degrees C. The thermophysical properties of the two types of PCM are characterized, revealing that the liquid metal is much more conductive while both have nearly identical volumetric latent heat of fusion (similar to 215 MJ/m(3)). By using at the same volume of 80 mL, i.e., the same energy storage capacity, the liquid metal is shown to outperform significantly over the organic PCM under the various heating powers up to 105.3 W/cm(2). During the heating period, the use of the liquid metal leads to a remarkable extension of the effective protection time to nearly twice longer as well as a reduction of the highest overheating temperature by up to 50 degrees C. The cool-down period can also be shortened significantly by taking advantage of the much higher thermal conductivity of the liquid metal. These findings suggest that liquid metals could serve as a promising PCM candidate for particular applications where the volume limit is very rigorous and the penalty in weight increment is acceptable. (C) 2016 Elsevier Ltd. All rights reserved.

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Journal Article

Abstract  In this work, a new thermodynamic method, based on the McMillan-Mayer solution theory, is proposed to interpret and predict the solubility of low- and high-molecular-weight compounds in compressed CO2. In the thermodynamic approach presented here, the solute is referred to as a pseudo pure component while the compressed CO2 is represented as a continuous medium that affects the interactions among solute molecules. The perturbed-hard-sphere-chain (PHSC) theory is used within the McMillan-Mayer framework to derive an expression for the repulsive and attractive contributions to the Helmholtz free energy of the solute.

While easy to handle, the model enlightens the effects of molecular weight and other physical-chemical characteristics on compounds solubility in compressed media. The thermodynamic approach fairly describes the experimental data concerning the solubility of several substances in compressed CO2 at different temperatures. The model also predicts CO2 solubility in PEG polymer and semi-quantitatively reproduces high-molecular-weight component solubility in compressed CO2 containing low amount of ethanol as co-solvent. (C) 2002 Elsevier Science B.V. All rights reserved.

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Journal Article

Abstract  The localized surface plasmon resonance (LSPR) behavior of indium-doped ZnO (IZO) nanocrystals synthesized in different solvents was studied. 1-octadecanol, oleic acid, oleyl alcohol, oleyl amine and 1-octadecene were used as solvent(s) and co-solvent(s) in the pyrolysis synthesis of indium-doped ZnO (IZO) nanoparticles. The results showed that the nanocrystals from a solvent system consisting of 1-octadecene, 1-octadecanol, and oleic acid exhibited enhanced LSPR near-infrared radiation absorption without sacrificing transparency in the visible region. The indium-rich core verified using ICP and XPS analysis was shown to be critical for the enhancement. The reaction mechanism of solvents on the generation of indium-rich core was elucidated through a systematic study of the reaction parameters. The interaction between the activating agent, inhibiting agent and solvent, and their effect on tuning the reactivity of dopant and host precursors were important for the formation of a nanostructure with a dopant-rich core. The solvent effect was also found in the synthesis of gallium-doped ZnO and confirmed to be a general phenomenon in the preparation of doped ZnO nanoparticles.

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Journal Article

Abstract  ES-285(.)HCl [(2S,3R)-2-amino-3-octadecanol hydrochloride] is a novel investigational anticancer agent, which has shown in vitro and in vivo cytotoxic activity against various tumor cell lines with selectivity for certain solid tumors. The pharmaceutical development of ES-285(.)HCl warranted the availability of an assay for the quantification and purity determination of ES-285(.)HCl active pharmaceutical ingredient (API) and its pharmaceutical dosage form. A liquid chromatographic method (LC) comprising of derivatisation of ES-285(.)HCl with phenylisothiocyanate and UV-detection was developed. The method was found to be linear, precise and accurate. The assay also proved selectivity as determined by analysing ES-285(.)HCl in combination with 15 analogues and in combination with hydroxypropyl-beta-cyclodextrin, the excipient used in the lyophilised pharmaceutical dosage form. Stress testing showed that the degradation products were separated from the parent compound, confirming its stability indicating capacity. The method was found robust as determined with design of experiments (DoE), which made it possible to predict system suitability responses in worst case experimental conditions and to define criteria for system suitability testing. (C) 2003 Elsevier B.V. All rights reserved.

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