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At least 19 recordsLinked to original sources
PubMed2005

Preferential solubilization of dodecanol from dodecanol-limonene binary oil mixture in sodium dihexyl sulfosuccinate microemulsions: effect on optimum salinity and oil solubilization capacity.

Solubilization of dodecanol-limonene binary oil mixtures has been studied in saturated Winsor type I and III sodium dihexyl sulfosuccinate microemulsions. The systems showed different oil solubilization behavior below and above dodecanol volume fraction 0.2. Below 0.2 dodecanol volume fraction regular Winsor type microemulsions formed. The oil solubilization was characterized in this concentration range by the optimum salinity and the maximum characteristic length. Dodecanol showed Langmuirian-type surface excess adsorption at the vicinity of the surfactant layer. Variation of the optimum salinity and middle phase characteristic length with increasing dodecanol concentration could be linked to changes in the dodecanol surface excess. These relationships were used to develop new mathematical models for the optimum salinity and characteristic length as a function of oil phase composition. Both models yield excellent agreement with the data. Above dodecanol volume fraction 0.2 regular Winsor type III microemulsions are not formed. Therefore our new models are not applicable in this concentration range.

Journal Article↗
PubMed2004

Preparation of dodecanol-tolerant strains of Yarrowia lipolytica.

Dodecanol (1% v/v) and dodecanoic acid (1% w/v) inhibited growth of Yarrowia lipolytica in complex media supplemented with glucose but dodecanedioic acid (1% w/v) was not toxic. Dodecanol-tolerant strains were prepared from the wild type strain H222 as well as the acyl-CoA oxidase deleted (deltaPOX2, POX3, POX5) strain MTLY35. These strains grew in rich media containing up to 10% (v/v) dodecanol. Dodecanol-tolerant strains remained dodecanol tolerant after they had been cultured in rich media without dodecanol. No significant amount of dodecanedioic acid was accumulated by the dodecanol-tolerant strains when grown on glucose in the presence of dodecanol.

Acyl-CoA Oxidase↗
PubMed2007

Characteristics of wormlike pentaoxyethylene decyl ether C(10)E(5) micelles containing n-dodecanol.

The wormlike micelles formed with the surfactant pentaoxyethylene decyl ether C10E5 containing n-dodecanol were characterized by static (SLS) and dynamic light scattering (DLS) experiments. The SLS results have been analyzed with the aid of the light scattering theory for micelle solutions, thereby yielding the molar mass Mw(c) as a function of concentration c along with the cross-sectional diameter d of the micelle. The observed Kc/DeltaR0 as a function of c and the hydrodynamic radius RH as functions of Mw have been well described by the theories for the wormlike spherocylinder model. It has also been demonstrated that the apparent hydrodynamic radius RH,app(c) as a function of c is well described by a fuzzy cylinder theory which takes into account the hydrodynamic and direct collision interactions among micelles. Our previous results for the hexaoxyethylene dodecyl ether C12E6 micelles containing n-dodecanol were reanalyzed in the same scheme. It has been found that the micellar length increases with increasing concentration c or with raising temperature T irrespective of the composition of the C10E5 + n-dodecanol and C12E6 + n-dodecanol systems. The length of the micelles at fixed c and T steeply increases with increasing weight fraction wd of n-dodecanol in both systems. The growth of the micelles accompanies the increase of the cross-sectional diameter d of the micelles and the results that the surfactant molecules are more densely assembled with increasing wd in order to keep n-dodecanol molecules inside the micelles.

Journal Article↗
PubMed1981

Omega- and (omega-1)-hydroxylation of 1-dodecanol by frog liver microsomes.

Frog liver microsomes catalyzed the hydroxylation of 1-dodecanol into the corresponding omega- and (omega-1)-hydroxy derivatives. The hydroxylation rate for 1-dodecanol was much lower than that for lauric acid. Both NADPH and O2 were required for hydroxylation activity. NADH had no effect on the hydroxylation. The hydroxylating system was inhibited 49% by CO at a CO:O2 ratio of 4.0. The formation of omega-hydroxydodecanol was more sharply inhibited by CO than was the formation of (omega-1)-hydroxydodecanol, implying that more than one cytochrome P-450 was involved in the hydroxylation of 1-dodecanol and that CO has a higher affinity for the P-450 catalyzing the omega-hydroxylation. The formation of laurate during the incubation of 1-dodecanol with frog liver microsomes suggests that a fatty alcohol oxidation system is also present in the microsomes. NAD+ was the most effective cofactor for the oxidation of 1-dodecanol and NADP+ had a little effect. Pyrazole (an inhibitor of alcohol dehydrogenase) had a slight inhibitory effect on the oxidation and sodium azide (an inhibitor of catalase) had no effect.

Animals↗
PubMed2004

Inclusion complexes of V-amylose with undecanoic acid and dodecanol at atomic resolution: X-ray structures with cycloamylose containing 26 D-glucoses (cyclohexaicosaose) as host.

Crystal structures are reported of cycloamylose containing 26 D-glucose residues (CA26, cyclohexaicosaose, C156H260O130) in complexes with undecanoic acid (CA26 x 2C10H21COOH x 34.95 H2O, orthorhombic P2(1)2(1)2(1), one CA26 and two bound undecanoic acids F1 and F2 in the asymmetric unit, resolution 0.95 angstroms) and with dodecanol ((CA26)(0.5) x C12H25OH x 32.0H2O, monoclinic C2, half a CA26 binding one dodecanol, A, in the asymmetric unit, resolution 1.0 angstroms). The macrocycle of CA26 is folded like the figure '8' into two 10 D-glucoses long left-handed V-amylose helices forming approximately 5A wide V-channels that are occupied by undecanoic acid (F1, F2) or dodecanol (A) as guest molecules. The functional head groups of the guests near the O(6) ends of the V-channels are hydrogen bonded with d-glucose O(6)n-H; the aliphatic termini beyond C(9) protrude from the O(2), O(3) ends. Parts of the aliphatic chains enclosed in the V-channels are all-trans except for one torsion angle each (approximately 130 degrees ) in undecanoic acid molecules F1 and F2. There are several (guest)C-H...O hydrogen bonds to O(4) and O(6) of CA26 in both complexes, and H...H van der Waals interactions with d-glucose C(3)-H and C(5)-H dominate. C(5)-H determine the position of the aliphatic chains of undecanoic acid F1 and of dodecanol A in contrast to F2 where both C(3)-H and C(5)-H contribute equally, probably because the V-channel is narrower than in F1 and in dodecanol. Complexes of polymeric V-amylose with fatty acids and alcohols studied by X-ray fiber diffraction could not provide the here described high resolution.

Amylose↗
PubMed2007

Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent.

Anethole shows synergistic effects on the antifungal activities of phytochemicals including polygodial and (2E)-undecenal against Saccharomyces cerevisiae and Candida albicans. It was found that a fungistatic dodecanol combined with a sublethal amount of anethole showed a fungicidal activity against S. cerevisiae. The MIC of dodecanol quickly reduced cell viability, but the cell viability recovered shortly after and then finally became no longer different from the control, indicating that the effect of dodecanol on this yeast was classified as sublethal damage. On the other hand, anethole completely restricted the recovery of cell viability. Therefore the expression of the synergistic effect was probably due to a blockade of the recovery process from dodecanol-induced stress.

Allylbenzene Derivatives↗
PubMed2005

Biological effect of 1-dodecanol in teneral and post-teneral Rhodnius prolixus and Triatoma infestans (Hemiptera: Reduviidae).

Topical application of 1-dodecanol was significantly more toxic against teneral first nymphs (1-3 h old) than post-teneral first nymphs (24 h old). The lethal dose ratios were 711,500 for Rhodnius prolixus and 3613 for Triatoma infestans. No significative difference between LD50 was found when 1-dodecanol was injected in recently hatched adult R. prolixus (1-4 h old) nor in older adults (24 h old). These values were similar to those calculated for deltamethrin (an effective triatomicide), showing that 1-dodecanol had no insecticidal properties when it was applied by injection. Topical application of high dose of 1-dodecanol (1 microg/i) on teneral first nymphs of R. prolixus, produced an interruption of the darkening process of the cuticle, and probably in the development of its physiological properties.

Animals↗
PubMed2005

[In vitro transdermal permeation of lidocaine-dodecanol binary eutectic system].

AIM: To study the effect of lidocaine-dodecanol binary eutectic system on the transdermal permeation of lidocaine. METHODS: Binary eutectic mixture of different proportions of lidocaine and dodecanol were prepared and the patch containing the binary eutectic mixture was developed. The solubilities of pure lidocaine and lidocaine from the binary eutectic system were determined in pH 7.9 phosphate buffer. The transdermal flux of lidocaine from the patches containing the binary eutectic system and pure lidocaine were measured using Franz-type single diffusion cell. RESULTS: The melting point of the lidocaine-dodecanol binary eutectic system was markedly lower than that of pure lidocaine. The steady state transdermal flux of lidocaine from the patch of the binary eutectic system was six times as much as that of pure lidocaine patch. CONCLUSION: The lidocaine-dodecanol binary eutectic system could produce high thermodynamic activity of the drug and the high driving force for transdermal permeation of lidocaine.

Administration, Cutaneous↗
PubMed1997

Ternary Phase Equilibria of the 1-Dodecylpyridinium Bromide-Dodecanol-Water System.

The isothermal ternary phase diagram for the 1-dodecylpyridinium bromide (1-DPB)-water-dodecanol system was determined at 40 degreesC, using 2H NMR, polarizing microscopy, and SAXS methods. All of the phases were characterized, and their ranges of existence were determined. The surfactant is easy to dissolve in water, yielding a normal micellar solution phase. After the normal micellar phase, on the binary surfactant-water axis, a normal hexagonal liquid crystalline phase is found at higher surfactant concentrations. On addition of dodecanol, four more phases are formed, i.e. a cubic, a lamellar, and a reverse hexagonal phase, followed by a reverse micellar solution phase. The lamellar liquid crystalline phase dominates the ternary phase diagram. The structures of the liquid crystalline phases were further examined using SAXS measurements, and the results are discussed in terms of the critical packing parameter, cpp, and electrostatic forces. The SAXS experiments show a pronounced swelling of the rods in the hexagonal phase, from 28.5 to 33 Å on addition of dodecanol, whereas the cylindrical aqueous core of the reverse hexagonal phase has a diameter of 18-21 Å, depending on sample composition. The average bilayer thickness of the lamellar phase is about 24 Å. Copyright 1997 Academic Press.

Journal Article↗
PubMed2005

Production of the long-chain alcohols octanol, decanol, and dodecanol by Escherichia coli.

As a follow-up to earlier studies on the emission of long-chain alcohols from broth cultures of Gram-negative enteric bacteria, E. coli was examined for the production of 1-octanol, 1-decanol, and 1-dodecanol. Ten strains of E. coli cultured in tryptic soy broth were assayed for volatile metabolites using solid-phase microextraction. Long-chain alcohols were produced by all strains with 1-decanol predominating with production ranging from 23.6 ng mL(-1) to 148 ng mL(-1). The production of long-chain alcohols followed the onset of the exponential growth phase of the broth culture. Doubling the concentration of glucose (5 g L(-1)) in the broth had no effect on the concentration of long-chain alcohols produced. Addition of octanoic, decanoic, or dodecanoic acids (as K(+) salts) to the broth (100 mg L(-1)) markedly increased the production of the corresponding alcohols by E. coli, ranging from a 13-fold increase for decanol to a 51-fold increase for dodecanol. However, decanol remained the predominant alcohol detected in all assays. These neutral volatile alcohols may have application as vapor-phase indicators for certain classes of bacteria, particularly, Gram-negative enteric bacteria.

Chromatography, Gas↗
PubMed2004

Adsorption and surface rheology of n-dodecanol at the water/air interface.

Adsorption layers of n-dodecanol at the water/air interface show phase transitions at low temperatures [Vollhardt, Fainerman, Emrich, J. Phys. Chem. B 104 (2000) 8536]. Using a drop shape technique it is shown that the dilational elasticity disappears in the coexistence region of the adsorption layer. The relaxation time between the condensed and liquid-like surface states is in the sub-second time range.

Adsorption↗
PubMed1996

Effect of EO Chain Length of Dodecanol Ethoxylates (C12En) on the Complexation of C12En/SDS Mixed Micelles with an Oppositely Charged Polyelectrolyte

Turbidimetry, dynamic light scattering, and capillary electrophoresis were used to study the complexation of polydiallyldimethylammonium chloride (PDADMAC) with mixed micelles of sodium dodecyl sulfate (SDS) and dodecanol ethoxylates (C12En). The effect of EO chain length and its distribution was examined using various combinations of C12En (n = 4, 6, 8, 12). The results show that the onset of the complexation of PDADMAC with the mixed micelles is affected by the EO chain length of C12En: the mole fraction (Y) of SDS in the mixed micelle required to form the complex (Yc) increases with n. The effect of EO chain length on the onset of bulk phase separation shows the same trend. Although Yc varies with n, the electrophoretic mobility of mixed micelles with composition corresponding to Yc is independent of n. We propose that the effect of EO chain length has two aspects: (1) an increase in the average distance between bound polycation segments and the SDS sulfate groups, and (2) an increase in the distance between SDS head groups, which causes a decrease in the surface charge density (sigma) of the micelle. Therefore, the electrical potential at the mean locus of bound polymer segments, psi0, decreases with increasing n; in order for complexation to occur, this effect must be compensated for by a larger value of Y. Broader distributions of EO chain length lead to an increase in the range of Y over which the soluble complex is stable. We suggest that polycations initially bind to micelles which are rich in shorter EO chains and thus have higher "surface" potential, psi0. However, additional SDS may go preferentially into micelles rich in longer chains with lower psi0. This delays the formation of micelles which have sufficiently large psi0 to cause phase separation.

Journal Article↗
PubMedDate not supplied

Airway responsiveness of rabbits after exposure to 2-octyl dodecanol.

Cooling lubricants are used in the metal industry during drilling or turning. Vapors and aerosols of these lubricants are suspected to induce airway hyperresponsiveness (AHR) in exposed workers. In a previous study the authors demonstrated that water-soluble lubricants induce AHR after acute exposure of rabbits to concentrations near the German MAK value (10 mg/m(3)). In the present investigation the influence of a fatty alcohol as special non-water-soluble cooling lubricant was examined to determine its influence on airway responsiveness (AR). The effects of an aerosolized non-water-soluble lubricant (40, 90, and 220 mg/m(3)) on AR to acetylcholine in a rabbit model were studied. Lubricant atmosphere analysis was performed with infrared spectroscopy. Before exposure, after 2 and 4 hours of application, AR to aerosols from 0.2 and 2% acetylcholine was tested. Basal airway and cardiovascular parameters as well as blood gases did not change during exposure. Lubricant aerosol concentration of 40 and 220 mg/m(3) for 4 hours did not significantly alter AR. Inhalation of 90 mg/m(3) lubricant increased contractile response to ACH significantly. In contrast to formerly investigated water-soluble cooling lubricants, the examined non-water-soluble lubricant did not increase AR in concentrations near the MAK; however, in higher concentrations a significant (p<.05) increase was obtained.

Acetylcholine↗
PubMed2005

Final amended report on the safety assessment of Octyldodecyl Stearoyl Stearate.

Octyldodecyl Stearoyl Stearate is an ester that functions as a skin-conditioning agent and viscosity-increasing agent. It is reported to be used in 105 cosmetic products at concentrations from 2% to 15%. In an isolated human skin permeation and penetration study, 0.005% of the applied dose permeated the skin, around 3% was found in the epidermis, around 1.5% was in tape stripped skin layers, and around 95% stayed in the material applied to the skin. A formulation having 20.6% Octyldodecyl Stearoyl Stearate was classified as minimally to mildly irritating in an in vitro ocular irritation assay. Several tests of products containing from 7.5% to 12.7% Octyldodecyl Stearoyl Stearate using rabbits produced minimal to mild ocular irritation. One test of 100% Octyldodecyl Stearoyl Stearate (a trade compound) and another of 10% Octyldodecyl Stearoyl Stearate in corn oil using rabbits produced no ocular irritation. Tests using rabbits demonstrated that Octyldodecyl Stearoyl Stearate at use concentrations was non- to mildly irritating to skin; only one study reported moderate irritation. Octyldodecyl Stearoyl Stearate was not mutagenic, with or without S-9 activation, in an Ames test and did not produce a significant increase in micronucleated cells in a mouse in vivo study. In clinical single-insult patch tests at use concentrations, Octyldodecyl Stearoyl Stearate was nonirritating to mildly irritating; in a cumulative irritation study, it caused mild irritation. Octyldodecyl Stearoyl Stearate was nonsensitizing in clinical tests. Because few toxicity data were available on Octyldodecyl Stearoyl Stearate, summaries of data from existing safety assessments of related ingredients (Octyl Dodecanol, Stearic Acid, and Octyl Stearate) were included. Undiluted Octyl Dodecanol was nontoxic during acute oral and dermal studies using rats and guinea pigs. Stearic Acid was nontoxic to rats during acute oral studies, but caused toxicity during subchronic studies. Rabbits treated topically with the acid were not affected adversely, and mild erythema and slight induration were observed when Stearic Acid was administered intradermally to guinea pigs and rabbits. Octyl Stearate had very low acute oral toxicity in rats and mice. Octyl Dodecanol produced only transient mild ocular irritation in rabbits when administered at concentrations up to 100%. Octyl Dodecanol (30% and 100%) was nonirritating to skin in one study using rabbits. In another study using multiple species, 100% Octyl Dodecanol (described as technical grade) caused severe skin irritation in rabbits, moderate irritation in guinea pigs and rats, and no irritation in swine. Stearic Acid was non- to moderately irritating in animal studies, and did not cause photosensitization. In studies using rabbits, undiluted Octyl Stearate caused slight, transient ocular irritation, and minimal skin irritation. Stearic Acid did not induce mitotic crossovers and aneuploidy in Saccharomyces cerevisiae, and was nonmutagenic in the Ames test. In a feeding study using mice, Stearic Acid was noncarcinogenic at doses up to 50 g/kg/day. Mice given subcutaneous injections of the acid had low incidences of carcinomas, sarcomas, and lymphomas. In clinical studies, concentrations of up to 100% Octyl Dodecanol were non- to mildly irritating, nonsensitizing, nonphototoxic, and nonphotosensitizing. Stearic Acid was nonirritating at concentrations up to 100%, and at concentrations up to 13% it was nonsensitizing and nonphotosensitizing. Octyl Stearate (7.6%) in formulation was nonirritating, nonsensitizing, and nonphotosensitizing. Based on skin permeation and penetration data, the Panel does not expect any significant amount of Octyldodecyl Stearoyl Stearate to be systemically available. There is no evidence of systemic toxicity associated with any of the related chemicals reviewed in previous safety assessments. None of the available toxicology or clinical data suggest a concern about adverse skin reactions to Octyldodecyl Stearoyl Stearate, or to any of the related chemicals. There is no evidence of ocular toxicity, except for a mild, transient ocular irritation associated with Octyldodecyl Stearoyl Stearate and the related chemicals. Overall, Octyldodecyl Stearoyl Stearate was considered safe as used in cosmetics.

Animals↗
PubMed2005

Mixtures of sodium dodecyl sulfate/dodecanol at the air/water interface by computer simulations.

Molecular dynamics simulations of monolayers of surfactant mixtures at the air/water interface were performed where the binary mixture was composed of sodium dodecyl sulfate (SDS) and dodecanol molecules. At the same ratio of SDS and dodecanol molecules, two monolayer mixtures were prepared. In the first monolayer, all the dodecanol molecules were placed together in the center of the simulation box, whereas in the second monolayer, those molecules were uniformly distributed in the surface area in such a way that they were far from each other. Simulations of both systems indicate that the dodecanol tails in the first monolayer are straighter and more ordered than those in the second monolayer. From the present results, we observed new insights of how the different molecules should array or distribute at the interface in real systems. Finally, studies of the interfacial water around the different surfactants were also analyzed, showing that they are closer to the polar headgroups of dodecanol than to the SDS headgroups.

Journal Article↗
PubMed1992

The effects of sodium lauryl sulphate and its oxidative breakdown products on calcium phosphate precipitation and transformation.

Most commercial dentifrices contain sodium lauryl sulphate, which oxidizes upon storage. The effects of aged sodium lauryl sulphate and its oxidative breakdown products on the conversion of amorphous calcium phosphate to hydroxyapatite were studied in vitro by a pH drop method. Hydroxyapatite was identified from its X-ray diffraction pattern. With storage time, the concentration of dodecanol [CH3(CH2)11OH], a breakdown product of sodium lauryl sulphate, increased. The storage dodecanol-containing sodium lauryl sulphate accelerated the conversion of amorphous calcium phosphate to hydroxyapatite. Dodecanol mixed with sodium lauryl sulphate accelerated the conversion when added both before and after initial formation of amorphous calcium phosphate. A stored commercial dentifrice also accelerated the conversion of amorphous calcium phosphate to hydroxyapatite. It was found that the concentration of dodecanol increased 2-fold over a 2-month period.

1-Butanol↗