Fatty Alcohols

Project ID

2760

Category

OPPT

Added on

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

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Journal Article

Abstract  Noncontact thermometry based on the fluorescence excitation spectrum of aqueous Eu(3+) (EDTA) near 579 nm allows us to measure the temperature of an evaporating drop of water. The results for drop diameters in the 500-microm-3-mm range confirm theoretical temperature predictions for steady state evaporation. Calibration of the excitation spectrum in a constant temperature cell indicates that +/-1.0 degrees C resolution is possible for temperatures below 20 degrees C. The spectrum depends only on the solution temperature when Eu(3+) (EDTA) concentrations are below 1 x 10(-3) M and when the solution pH is between 4.0 and 10.0. Excitation spectra from levitated waterdrops contain additional noise which degrades the temperature resolution to +/-1.2 degrees C. With this technique we are able to follow the temperature change in an evaporating drop of water as a monolayer of 1-octadecanol forms on the surface and retards the evaporation.

Journal Article

Abstract  Extractive fermentation has been proposed to enhance the productivity of fermentations that are end product inhibited. Unfortunately, good extractants for butanol, such as decanol, are toxic to Clostridium acetobutylicum. The use of mixed extractants, namely, mixtures of toxic and nontoxic coextractants, was proposed to circumvent this toxicity. Decanol appeared to inhibit butanol formation by C. acetobutylicum when present in a mixed extractant that also contained oleyl alcohol. However, maintenance of the pH at 4.5 alleviated the inhibition of butanol production and the consumption of butyrate during solventogenesis. A mixed extractant that contained 20% decanol in oleyl alcohol enhanced butanol formation by 72% under pH-controlled conditions. The production of acetone and acetoin was also increased, even though these two products were not extractable. The enhancement of butanol formation was not limited by the toxicity of decanol. Supplementation of glucose and butyrate in the extractive fermentation yielded a 47% increase in butanol. The enhancement of butanol formation appeared to be dependent on the presence of dissolved decanol in the broth but was not observed unless an organic phase was present to extract butanol. A mechanism for the effects of decanol on product formation is proposed.

Journal Article

Abstract  Mathematical formulation was made for the performance evaluation of extractive fermentation using multiple solvents. Two types of solvent-supplying strategies were considered. One is to add multiple solvents simultaneously and the product is removed at one time. Another is to add them one by one consecutively. Computer simulation was made for batch, fed-batch, and repeated fed-batch operation of acetone-butanol fermentation to show the power of the approach. The result shows that the significant performance improvement in terms of the productivity and the product concentration is expected when two extractants such as oleyl alcohol and benzyl benzoate are used as compared with the case of using only one solvent.

Journal Article

Abstract  Addition of oleate, oleyl alcohol, or palmitate to HeLa cell medium resulted in a rapid stimulation of PC synthesis and activation of CTP: phosphocholine cytidylyltransferase. Stimulation was optimal with 0.35 mM oleate, 0.3 mM oleyl alcohol and 5 mM palmitate, or 1 mM palmitate if EGTA were added to the medium. The cytidylyltransferase was activated by translocation of the inactive cytosolic form to membranes. In untreated cells approx. 30% of the total cytidylyltransferase was membrane bound, while in treated cells, 80-90% was membrane associated. Addition of bovine serum albumin (10 mg/ml) to cells previously treated with oleate (0.35 mM) rapidly removed cellular fatty acid, and the membrane-bound cytidylyltransferase activity returned to approx. 30%. Similar results were obtained by extraction of membranes with albumin in vitro. Although 95% of the free fatty acid was extracted, 30-40% of the membrane cytidylyltransferase remained bound. Translocation of cytidylyltransferase between isolated cytosol and microsomal fractions was promoted by addition of oleate, palmitate, oleyl alcohol, and monoolein. Addition of diacylglycerol, lysophosphatidylcholine, lysophosphatidylethanolamine, calcium palmitate, and detergents such as Triton X-100, cholate or Zwittergent did not stimulate translocation of the enzyme. Addition of oleoyl-CoA promoited translocation, however, 40% of it was hydrolyzed releasing free oleic acid. Cytosolic cytidylyltransferase bound to microsomes pre-treated with phospholipase C, which had 7-fold elevated diacylglycerol content. Fatty acid-promoted translocation was blocked by Triton X-100, but not by 1 M KCl. These results suggest that a variety of compounds with differing head group size and charge, and number of hydrocarbon chains can function as translocators, and that hydrophobic rather than ionic interactions mediate the binding of cytidylyltransferase to membranes.

Journal Article

Abstract  Three compounds have been identified in the abdominal tip extracts from the female leopard moth,Zeuzera pyrina L. Gas-liquid chromatography and mass spectroscopy data showed that (E, Z)-2, 13-octadecadien-1-ol acetate was the main component and that (Z)-13-octadecen-1-ol acetate and octadecan-1-ol acetate were secondary components. The electroanten-nographic responses of maleZ. pyrina to nanogram amounts of all four 2, 13-octadecadien-1-ol acetate isomers indicated that theE, Z isomer had the maximum activity. A strong EAG response was also recorded for (Z)-7-do-decen-1-ol acetate, which was not detected in the female extracts.

Journal Article

Abstract  A simultaneous extraction-stripping process is proposed for separating volatile products from fermentation broths, it is based on pervaporation through a liquid membrane supported with a hydrophobic porous membrane. The liquid membrane prepared with oleyl alcohol was selected as the most suitable for separating volatile products resulting from acetone-butanol fermentation. The separation performance and stability of the oleyl alcohol liquid membrane were investigated by using dilute aqueous butanol and acetone solutions. The oleyl alcohol liquid membrane was found to be superior by far in both selectivity and permeability of butanol to the better known silicone rubber membrane in its high selectivity for alcohols. Using the oleyl alcohol liquid membrane, the dilute aqueous butanol solutions of around 4 g/L obtained in acetone-butanol fermentation could be concentrated up to 100 times. The stability of this liquid membrane was also quite good as long as the surface tension of the feed solution was less than the critical surface tension of the support membrane. No change in the separation performance was found after the continuous usage in a long period of 100 h.

Journal Article

Abstract  Ethanolamine plasmalogen radiolabelled mainly in the O-alkenyl moiety was prepared from cell suspension cultures of the flagellate Leishmania donovani previously incubated with [1-14C]octadecanol over one growth period. The optimal concentration of [1-14C]octadecanol for labelling was shown to be 1 microM, when 60% of total lipid radioactivity appeared in the 1,2-diradyl-sn-glycero-3-phosphoethanolamine fraction, with an overall yield of approx. 35%. Analysis of this fraction revealed that 93% of the label was present in O-octa-dec-1-enyl, 3% in O-alkyl and 4% in acyl moieties. A specific radioactivity of approx. 14 mCi/mmol was determined. Raising the culture medium concentration of [1-14C]octadecanol to 2 microM yielded a product with a specific radioactivity of 25 mCi/mmol.

Journal Article

Abstract  After growth and experimental conditions were established, the mycolic acid cleavage products, constituent fatty acids, and alcohols of representative strains of Mycobacterium tuberculosis, M. smegmatis, M. fortuitum complex, M. kansasii, M. gordonae, and M. avium complex were determined by capillary gas chromatography. Reproducible cleavage of mycolic acid methyl esters to tetracosanoic (24:0) or hexacosanoic (26:0) acid methyl esters was achieved by heating the sample in a high-temperature muffle furnace. The major constituent fatty acids in all species were hexadecanoic (16:0) and octadecenoic (18:1 omega 9-c, oleic) acids. With the exception of M. gordonae, 10-methyloctadecanoic acid was found in all species; moreover, M. gordonae was the only species tested which contained 2-methyltetradecanoic acid. M. kansasii was characterized by the presence of 2,4-dimethyltetradecanoic acid, M. avium complex by 2-eicosanol, and M. tuberculosis by 26:0 mycolic acid cleavage product. The mycolic acid cleavage product in the other five species tested was 24:0. Although a limited number of strains and species were tested, preliminary results indicate that this gas chromatographic method can be used to characterize mycobacterial cultures by their mycolic acid cleavage products and constituent fatty acid and alcohol content.

Journal Article

Abstract  Synopsis The ternary mixtures investigated were obtained from water, mineral oil and ether-linked non-ionic surfactants (polyoxyethylene derivatives of oleic alcohol). The examination of the rheological properties of these mixtures, particularly the viscoelastic properties of the various phases encountered in these diagrams, was expanded. The phases examined were: - anisotropic paracrystalline phases: hexagonal phase and lamellar phase; - the isotropic paracrystalline phase: type I viscous isotropic phase. The measurement instrument used for this work was a creep rheometer. The paracrystalline phases were subjected to very low shear stresses, and the strains induced were recorded as a function of time. The analysis of creep functions obtained enabled us to construct a viscoelastic model and obtain the value of its parameters for each particular case. This analysis of the viscoelastic properties provides an accurate identification of each of the paracrystalline phases: the lamellar and isotropic viscous phases show respectively a Newtonian fluid nature with a yield value (Bingham model), and a perfect elastic solid. The hexagonal phase on the other hand shows an intermediate type of behaviour which is characterized by a well-defined retarded elasticity. This study could also lead to a microscopic interpretation of their structure.

Journal Article

Abstract  Oxyethylene docosanol (OED) retarded evaporation of agar media in petri plates when the plates were used in an air sampler; this confirmed the report of May (2). Flooding of plates with OED solutions or incorporation of OED into agar media, however, did not alter evaporation rates when the plates were stored in incubators or were refrigerated.

Journal Article

Abstract  Twenty-nine strains of chromogenic mycobacteria belonging to the species Mycobacterium aurum (5 strains), M. duvalii (2), M. flavescens (1), M. gordonae (6), M. kansasii (3), M. obuense (1), M. parafortuitum (3), M. phlei (2), M. rhodesiae (1), M. vaccae (2) and Mycobacterium spp. (3) were studied for fatty acid composition and mycolic acid patterns by gas-liquid chromatography and thin-layer chromatography respectively. Fatty acids found ranged from those with 12-24 carbon atoms and were saturated and monounsaturated straight chain fatty acids, along with 10-methyl branched of 16, 17 and 18 (tuberculostearic acid) carbon atoms. Moreover, 2-methyl tetradecanoic acid was found in M. gordonae, M. kansasii and Mycobacterium spp. (2 strains), and 2,4-dimethyl tetradecanoic acid in M. kansasii and Mycobacterium spp. (2 strains). Nonadecenoic acid was found only in M. flavescens and tuberculostearic acid was not detected in M. gordonae. Three patterns of mycolic acids were obtained: the first, found in M. aurum, M. flavescens, M. phlei, M. rhodesiae and Mycobacterium spp. (1 strain), was characterized by the presence of several spots assigned to alpha-mycolates, keto-mycolates and wax-ester mycolates (omega-carboxy-mycolates and 2-eicosanol and related alcohols); the second, found in M. duvalii, M. obuense, M. parafortuitum and M. vaccae was similar to the first, but it contained an additional spot of alpha'-mycolates; the third pattern, found in M. gordonae, M. kansasii and Mycobacterium spp. (2 strains) contained three spots considered to be alpha-mycolates, methoxy-mycolates and keto-mycolates. The results obtained confirm previously reported data on the fatty and mycolic acid composition of the species studied.

Journal Article

Abstract  Column chromatography of the pentane extract of freeze-dried cotton buds or anthers yielded a wax-sterol ester fraction that exhibited potent feeding stimulant activity for the cotton boll weevil. The waxes of the wax-sterol ester mixture were responsible for the feeding activity. Saponification of the wax-sterol ester fraction yielded about 15% alcohols and 85% sterols. A C18∶1 alcohol, dihydrophytol, phytol, and geranylgeraniol constituted 15, 36, 26, and 23%, respectively, of the total alcohols, implicating certain of their long-chain esters as feeding stimulants. Several esters of dihydrophytol, phytol, and geranylgeraniol were identified among the waxes by GC-MS. Certain phytol, geranylgeraniol, and oleyl alcohol esters containing C12 to C26 acid moieties were synthesized and were found to induce high feeding stimulant activity in the cotton boll weevil.

Journal Article

Abstract  Sphingosine has been shown to activate protein kinases in Jurkat T cell cytosol [Pushkareva, Khan, Alessenko, Sahyoun and Hannun (1992) J. Biol. Chem. 267, 15246-15251]. In this study, two sphingosine-activated protein kinases were distinguished by their substrate specificity, their dose-response to sphingosine and the specificity of their activation by sphingosine and dihydrosphingosine stereoisomers. A p32-sphingosine-activated protein kinase responded to low concentrations of D-erythrosphingosine with an initial activation observed at 2.5 microM and a peak activity at 10-20 microM. This kinase showed a modest specificity for D-erythro-sphingosine over other sphingosine stereoisomers, and a preference for sphingosines over dihydrosphingosines. Phosphorylation of a p18 substrate required higher concentrations of sphingosine (20-100 microM) and showed a significant preference for the erythro isomers of sphingosine and dihydrosphingosine over the threo isomers. The ability of other lipids to modulate sphingosine activation of these kinases was also examined. Oleic acid, but not oleic alcohol or the methyl ester, induced the phosphorylation of a distinct set of substrates (probably through the activation of protein kinase C), and inhibited sphingosine-induced phosphorylation with an IC50 of approximately 20 microM. Oleic anhydride failed to induce changes in basal protein phosphorylation but inhibited sphingosine-activated protein kinases, thus distinguishing the effects of fatty acids on protein kinase C from the inhibition of sphingosine-induced phosphorylation. These studies define two distinct sphingosine-activated protein kinases and reveal an important interaction between two classes of putative lipid second messengers.

Journal Article

Abstract  Objectives: To investigate the effects of terazosin and melatonin on isolated rabbit bladder strips after partial bladder outlet obstruction and determine responses to agonist-induced contractility and changes in oxidant-antioxidant system. Methods: We created partial bladder outlet obstruction in 5 groups of rabbits, each containing 8. Rabbits with sham operation (group 1) received no drug treatment. Similarly, animals in group 2 underwent partial bladder outlet obstruction and received no drug treatment. Rabbits in groups 3 were administered 5 mg/day oral terazosin, and rabbits in group 4 received 10 mg/kg/day melatonin intraperitoneally. Animals in group 5 received both terazosin and melatonin. We removed their bladders and performed histopathological and biochemical measurements. We assessed tissue malondialdehyde and antioxidant enzyme activity levels and recorded in vitro contractility response to KCl in isolated organ baths. Results: The thickness of muscularis propria was significantly increased in group 2 compared with all other groups. KCl-evoked contractions after partial outlet obstruction were significantly impaired in group 3 and 4 animals receiving terazosin and melatonin, respectively. However, combined use of melatonin and terazosin in group 5 showed contractility responses similar to sham-operated animals (P <0.05). Melatonin administration to groups 4 and 5 showed decreased levels of lipid peroxidation. Similarly, animals receiving melatonin and melatonin plus terazosin showed statistically significant increase in antioxidant enzyme activities. Conclusions: In the present study, we showed that oxidative stress induced by partial bladder outlet obstruction can be successfully antagonized by the potent antioxidant melatonin, and its combined use with an alpha-antagonist such as terazosin may restore in vitro contractility. [Copyright 2008 Elsevier] Copyright of Urology is the property of Excerpta Medica Publishing Group and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts)

Journal Article

Abstract  BIOSIS COPYRIGHT: BIOL ABS. The application of Salmonella/microsomal mammalian tests to column chromatography fractions isolated from river and marine sediments collected in the vicinity of Barcelona City, Spain, demonstrated a positive response (TA98+S9 mix) among the polar fractions. Chemical analysis by high resolution gas chromatography coupled to negative ion chemical ionization mass spectrometry (HRGC-NICI MS) provided sensitivity and selectivity to detect several mutagenic chemical classes. Among them, nitrated PAHs, azaarenes, aromatic amines, anhydrides, and ketones were identified. A total of 116 compounds were tentatively identified, 22 for the first time, of which 16 possessed mutagenic activity. However, a lack of correlation between chemical composition and fraction mutagenicity in the medium polarity fractions, especially in the river sediment, was evidenced. The occurrence of multiple interactions between components in spiked organic extracts is demonstrated.

WoS
Journal Article

Abstract  In order to obtain a novel prescription to treat scald, a new ointment was assessed. The ointment was made of pepsin soluble collagen (PSC), Bletilla striata polysaccharide (CBSP), lentinan, 1-octadecanol, dodecyl sodium sulfate, white vaseline, methyl hydroxybenzoate, propyl hydroxybenzoate, propylene glycol and distilled water. Experiment involving mice with their biochemical assays was used to evaluate the suitability of the ointment. The ointment which include by 1.5 g PSC, 1.5 g CBSP, 1.5 g lentinan, 20 g 1-octadecanol, 1.46 g dodecyl sodium sulfate, 23 g white vaseline, 0.025 g methyl hydroxybenzoate, 0.015 g propyl hydroxybenzoate, 11 g propylene glycol, and 40 g distilled water is optimal ointment. The scar outcomes rate all reach 100.00% in ointment group and model group. However, the ointment group of scar outcomes rate is higher than model group in the tenth day. The ointment 1, 2 and 3 group can significantly improve the activity of superoxide dismutase, increase the content of monoamine oxidase and reduce the content of malondialdehyde. The ointment had no influence on the body mass, the relative organ mass, blood hematology and serum biochemical indices of the mice. The results of the study indicated that the ointment can be used to treat scalds on mouse, increase the rate of the scar outcome and promote scald heal.

DOI
Journal Article

Abstract  Purpose: To ascertain the influence of paraffin, white soft paraffin and pre-hydrated white soft paraffin on the viscosity of a cream formulated with a corticosteroid. Methods: The formulations were prepared via homogenization with variable velocity in the range 3300 4000 rpm. Individual series of preparations contained the same proportion of macrogol cetostearyl alcohol, cetyl alcohol, stearyl alcohol, sorbitan stearate, propylene glycol, metyl parahydroxybenzoate, propyl parahydroxybenzoate and water. The semi-solid preparations were assessed by viscometric and microscopic methods. Results: The viscosity of the samples measured ranged from 13050 to 15660 mPas. The particles in dispersed phase sized from 15 to 90 mu m. Within the multiple emulsion, the continuous phase included fine particles with diameter < 5 mu m. Change of the liquid paraffin used from Ondina 934 to Vara 600P significantly decreased the viscosity of the formulation. Several phases within the formulations were distinguished microscopically. Increased viscosity was observed in formulations with increasing proportion of white soft paraffin. Conclusion: Both the ratio of liquid paraffin to white soft paraffin, as well as the initial hydration of white soft paraffin influenced the viscosity of the cream as well as the diameter of particles in the dispersed phase.

Journal Article

Abstract  π-A isotherms, atomic force microscopy (AFM), and sum frequency generation (SFG) vibrational spectroscopy are employed to investigate the molecular structure and lateral interactions in mixed monolayers of dioctadecyldimethylammonium chloride (DOAC) and stearyl alcohol (SA) at air/water and air/solid interfaces. To avoid possible interference between the two molecules in the SFG spectroscopic measurements, perprotonated DOAC and perdeuterated SA (dSA) were used. The thermodynamic analyses for the π-A isotherms show that DOAC is miscible with dSA. SFG observations reveal that DOAC molecules become conformationally ordered as dSA molecules are introduced into the monolayer. AFM observations demonstrate coexistence of DOAC-rich and dSA-rich domains in the mixed monolayer with ratios different from their initial composition in the subphase. The present study suggests that DOAC molecules in the mixed monolayer are condensed by mixing with dSA in which the repulsive interactions between positively charged head groups of the DOAC molecules are largely reduced along with an increase of van der Waals interactions with dSA.

Technical Report

Abstract  BIOSIS COPYRIGHT: BIOL ABS. RRM SYNTHESIS Z-11 HEXADECENOL Z-11 HEXADECENYL ACETATE Z-11 HEXADECENAL Z-13 OCTADECENOL Z-13 OCTADECENYL ACETATE Z-13 OCTADECENAL

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