[Halogenated derivatives of acyclic hydrocarbons and their effect on the liver].
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Ethylenes↗
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[Chlorinated derivatives of acyclic hydrocarbons; provisions concerning labeling of containers].
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Halogenation↗
Physicochemical characterization of tetraether lipids from Thermoplasma acidophilum. V. Evidence for the existence of a metastable state in lipids with acyclic hydrocarbon chains.
The main glycophospholipid of Thermoplasma acidophilum, grown at 39 degrees C, is composed of a di-isopranol-2,3-glycerotetraether. It has been characterized in hydrated systems by calorimetry. Unlike its equivalent grown at 59 degrees C, it shows complex phase properties, which include at least three different phases, (1) a liquid-analogue state (C), which is stable above 20 degrees C, (2) a metastable solid-analogue state (A) formed by supercooling of the liquid-analogue state (C) and (3) a stable solid-analogue state (B), which is slowly formed and may include a close chain packing of lipids and a network of hydrogen bonds between the headgroups. A high fraction of acyclic isopranol chains seems to be a prerequisite for the formation of state (B). A phase diagram, displaying the observed states and the transitions between them is proposed.
Calorimetry↗
Burial, exportation and degradation of acyclic petroleum hydrocarbons following a simulated oil spill in bioturbated Mediterranean coastal sediments.
A field study was conducted in a French Mediterranean littoral (Gulf of Fos) in order to determine the role of bioturbation processes during the bioremediation of oil-contaminated sediments. Inert particulate tracers (luminophores) and Arabian light crude oil were deposited at the surface of sediment cores incubated in situ for 2, 6 and 12 months. After incubation, luminophores and hydrocarbons presented roughly similar depth distributions in the sediment, showing a continuous burial of material until 55 mm depth. Short-chain (< or = n-C25) n-alkanes were totally removed from the sedimentary column after 6 months, whereas approximately 20% of heavier n-alkanes (e.g. n-C30) and of isoprenoid hydrocarbons (pristane (Pr) and phytane (Ph)) remained at the end of the experiment. The determination of the degradation constant and the turn-over rate of individual hydrocarbon indicated that C17-25 n-alkanes were degraded two to three times faster than longer homologues and than pristane and phytane. Using the 17alpha,21beta-C30-hopane as an internal inert reference, we could demonstrate that, after 12 months of in situ incubation, 55% of the losses of the n-alkanes < or = C25 and 35% of the losses of the heavier n-alkanes and of Pr and Ph were due to biodegradation processes. These results demonstrate that the activity of benthic organisms can have a significant influence on the qualitative and quantitative fate of acyclic hydrocarbons following a petroleum contamination in marine coastal sediments.
Animals↗
[Studies on the components in NTU shale oil. VIII. Identification of acyclic isoprenoid hydrocarbons (author's transl)].
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Chemical Phenomena↗
Metabolism and nephrotoxicity of indan in male Fischer 344 rats.
Indan, a component of fuels, solvents, and varnishes, is metabolized in male Fischer 344 rats to 1-indanol, 2-indanol, 5-indanol, 1-indanone, 2-indanone, 2-hydroxy-1-indanone, cis-1,2-indandiol, and trans-1,2-indandiol. The metabolites were identified using the techniques of gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The rats treated with indan demonstrated the classic lesions of hydrocarbon-induced nephropathy. The kidney damage produced was less than that found for tetralin and other branched-chain acyclic hydrocarbons.
Administration, Oral↗
New terpene hydrocarbons from the alligatoridae (crocodylia, reptilia).
The contents of the paracloacal gland secretions of the alligatorids Alligator mississippiensis, A. sinensis, Paleosuchus palpebrosus, and P. trigonatus were investigated. Novel acyclic hydrocarbon terpenes with a rare trisubstituted 2,4-diene system were identified in the secretions of A. sinensis, P. palpebrosus, and P. trigonatus. The structures of the monoterpene (2E,4E)-3,7-dimethyl-2,4-octadiene (9) and the sesquiterpene (2E,4E,7S)-3,7,11-trimethyl-2,4-dodecadiene (14) were proven by synthesis and gas chromatography on a chiral phase. Several other new terpenes (11, 16, 17, 18, 19, and 20) related to these components also were present in the secretions, as well as the known compounds myrcene (6), (E)-beta-farnesene (4), (E)-beta-springene (3), squalene (5), cembrene A (1), and 11,12-dihydrocembren-10-one (2).
Alligators and Crocodiles↗
Progressive systematic underestimation of reaction energies by the B3LYP model as the number of C-C bonds increases: why organic chemists should use multiple DFT models for calculations involving polycarbon hydrocarbons.
[reaction: see text] Computational studies of three different reaction types involving hydrocarbons (homolytic C-C bond breaking of alkanes, progressive insertions of triplet methylene into C-H bonds of ethane, and [2+2] cyclizations of methyl-substituted alkenes to form polymethylcyclobutanes) show that the B3LYP model consistently underestimates the reaction energy, even when extremely large basis sets are employed. The error is systematic and cumulative, such that the reaction energies of reactions involving hydrocarbons with more than 4-6 C-C bonds are predicted quite poorly. Energies are underestimated for slightly and highly methyl-substituted cyclic and acyclic hydrocarbons, so the errors do not arise from structural issues such as steric repulsion or ring strain energy. We trace the error associated with the B3LYP approach to its consistent underestimation of the C-C bond energy. Other DFT models show this problem to lesser extents, while the MP2 method avoids it. As a consequence, we discourage the use of the B3LYP model for reaction energy calculations for organic compounds containing more than four carbon atoms. We advocate use of a collection of pure and hybrid DFT models (and ab initio models where possible) to provide computational "error bars".
Journal Article↗
Thermotropic properties of dispersions of cholesterol with tetraether lipids from Thermoplasma acidophilum.
The main glycophospholipid from Thermoplasma acidophilum is composed of a diisopranol-2,3-glycerotetraether. The fraction of pentane cyclizations of its hydrocarbon chains increases with the growth temperature of the source organism (39-59 degrees C). Hydrated mixtures of these lipids together with cholesterol have been studied by calorimetry. With the reduction of the phase transition temperatures and enthalpy changes of the transitions, cholesterol is readily incorporated into lipid monolayers in the liquid-crystalline and the (metastable) solid-analogue phase. Lipid samples with a high number of acyclic hydrocarbon chains form a stable and a metastable solid-analogue phase. With the increasing concentration of cholesterol the metastable solid-analogue phase is stabilized and the time constant for the formation of the stable solid-analogue phase is prolonged.
Calorimetry, Differential Scanning↗
Hydrocarbon uptake by roots of Vicia faba (Fabaceae).
Vicia faba was grown in crude oil polluted soil and its roots were extracted for the detection and estimation of hydrocarbons. Saturated and unsaturated Aliphatic Hydrocarbons (AHs) ranging from C(22) to C(36) were identified in AHs fraction. However, PAHs were not present in the same extract. This could be due to the fact that PAHs being toxic compounds are not accumulated in the plant root extracts of V. faba grown in crude oil polluted soil. Three phytoalexins were identified and estimated by mass spectrometric analysis in the root extracts of V. faba. These three compounds are 2-t-butyl-4-(dimethyl benzyl) phenol, 2, 4-bis (dimethyl benzyl) phenol and 2,4-bis (dimethyl benzyl)-6-butyl phenol. These phenolics in V. faba are being reported for the first time. These compounds are presumably elicited as a direct stress on crude oil hydrocarbons on the roots of this plant.
Hydrocarbons↗
Modelling soot and SOF emissions from a diesel engine.
Modelling of soot and SOF emissions from a typical European turbocharged diesel engine has been made. The model consists of a detailed kinetic mechanism with 472 reactions (120 chemical species) and data from the thermodynamic diagnostic procedure of the combustion process of the engine. The forward kinetic constants were obtained from literature and the background constants from a self-developed non-linear fitting routine based on the Marquardt algorithm. The dilution and mixing processes inside the engine are represented by a simple Wiebe function. The system of ordinary differential equations is solved with the Rosenbrock method for rigid systems and using the interpolating Lagrange polynomials to calculate the heat capacity of each species at the corresponding temperature. The kinetic model has been implemented in Digital Visual Fortran 6.0. The model has been executed for five different fuels and three mixtures of biodiesel and reference diesel operating under three diverse conditions from the European transient urban/extraurban Certification Cycle and the results of soot and SOF predicted are compared with experimental data.
Air Pollutants↗
Fingerprinting petroleum hydrocarbons in plankton and surface sediments during the spring and early summer blooms in the Galician coast (NW Spain) after the Prestige oil spill.
Plankton samples (20-350 microm and >350 microm) collected at three transects along the Galician coast (NW Spain) were analysed for individual aliphatic and aromatic hydrocarbons by GC-MS. Sample collection was performed in April-July 2003, after the Prestige oil spill (November 2002), to determine whether the hydrocarbons released into the water column as a consequence of the spill were accumulated by the planktonic communities during the subsequent spring and early summer blooms. Surface sediments were also collected to assess the presence of the spilled oil, removed from the water column by downward particle transport. Plankton concentrations of PAHs (Sigma14 parent components) were in the range of 25-898 ng g(-1)dw, the highest values being close to coastal urban areas. However, the individual distributions were highly dominated by alkyl naphthalenes and phenanthrenes, paralleling those in the water dissolved fraction. The detailed study of petrogenic molecular markers (e.g. steranes and triterpanes, and methyl phenanthrenes and dibenzothiophenes) showed the occurrence of background petrogenic pollution but not related with the Prestige oil, with the possible exception of the station off Costa da Morte in May 2003, heavily oiled after the accident. The dominant northerly wind conditions during the spring and early summer 2003, which prevented the arrival of fresh oil spilled from the wreck, together with the heavy nature of the fuel oil, which was barely dispersed in seawater, and the large variability of planktonic cycles, could be the factors hiding the acute accumulation of the spilled hydrocarbons. Then, with the above exception, the concentrations of PAHs found in the collected samples, mostly deriving from chronic pollution, can be considered as the reference values for the region.
Animals↗
Aliphatic and aromatic hydrocarbons in marine biota and coastal sediments from the Gulf and the Gulf of Oman.
The composition and spatial distribution of aliphatic and polycyclic aromatic hydrocarbons (PAHs) were investigated in biota and coastal sediments from four countries surrounding the Gulf (Bahrain, Qatar, United Arab Emirates and Oman). The levels of total petroleum hydrocarbons (TPH), aliphatic unresolved mixture and PAHs in sediments and biota were relatively low compared to world-wide locations reported to be chronically contaminated by oil. Only in the case of the sediments collected near the BAPCO oil refinery in Bahrain, having concentrations of 779 microg g(-1) total petroleum hydrocarbon equivalents and 6.6 microg g(-1) Sigma PAHs, can they be categorized as chronically contaminated. Some evidence of oil contamination was also apparent in sediments and bivalves around Akkah Head and Abu Dhabi in the UAE, and near Mirbat in Oman. Contaminant patterns in sediments and biota indicated that the PAHs were mainly from fossil sources, with the exception of the high PAH concentrations in sediments near the BAPCO refinery that contained substantial concentrations of carcinogenic PAH combustion products.
Animals↗
A quantitative structure-toxicity relationships model for the dermal sensitization guinea pig maximization assay.
We have developed quantitative structure-toxicity relationship (QSTR) models for assessing dermal sensitization using guinea pig maximization test (GPMT) results. The models are derived from 315 carefully evaluated chemicals. There are two models, one for aromatics (excluding one-benzene-ring compounds), and the other for aliphatics and one-benzene-ring compounds. For sensitizers, the models can resolve whether they are weak/moderate or severe sensitizers. The statistical methodology, based on linear discriminant analysis, incorporates an optimum prediction space (OPS) algorithm. This algorithm ensures that the QSTR model will be used only to make predictions on query structures which fall within its domain. Calculation of the similarities between a query structure and the database compounds from which the applicable model was developed are used to validate each skin sensitization assessment. The cross-validated specificity of the equations ranges between 81 and 91%, and the sensitivity between 85 and 95%. For an independent test set, specificity is 79%, and sensitivity 82%.
Administration, Topical↗
Evaluation of a biologically active cover for mitigation of landfill gas emissions.
Landfills are the third largest source of anthropogenic CH4 in the United States, and there is potential for reduction in this source of greenhouse gases and other contaminants. The objective of this work was to contrast emissions of CH4 and non-methane organic compounds (NMOCs) from landfill cells covered with soil or a biologically active cover consisting of yard waste compost. On the basis of four field campaigns over 14 months, CH4 emissions from the biocover (BC) varied from -1.73 to 1.33 g m(-2) d(-1), with atmospheric uptake measured in 52% of tests. BC emissions did not increase when the gas collection system was turned off. Uptake of atmospheric CH4 was measured in 54% of tests on the soil cover (SC) when the gas collection was system active and 12% when the gas collection system was off. Many (26%) relatively high fluxes (>15 g m(-2) d(-1)) were measured from the SC as were some dramatic effects due to deactivation of the gas collection system. In tests with positive emissions, stable isotope measurements showed that the BC and SC were responsible for oxidation of 55% and 21% of the CH4 reaching the bottom of the respective cover. Seven of the highest 10 NMOC emissions were measured in the SC, and 17 of 21 fluxes for speciated organic compounds were higher in the SC. The relationship between CH4, NMOC, and individual organic compound emissions suggested a correlation between CH4 and trace organic oxidation. BCs can reduce landfill gas emissions in the absence of a gas collection system and can serve as a polishing step in the presence of an active system.
Air Pollutants↗
Mapping property distributions of molecular surfaces: algorithm and evaluation of a novel 3D quantitative structure-activity relationship technique.
A novel molecular descriptor called MaP (mapping property distributions of molecular surfaces) is presented. It combines facile computation, translational and rotational invariance, and straightforward interpretability of the computed models. A three-step procedure is used to compute the MaP descriptor. First, an approximation to the molecular surface with equally distributed surface points is computed. Next, molecular properties are projected onto this surface. Finally, the distribution of surface properties is encoded into a translationally and rotationally invariant molecular descriptor that is based on radial distribution functions (distance-dependent count statistics). The calculated descriptor is correlated with biological data through chemometric regression techniques in combination with a variable selection. The latter is used to identify variables that are highly relevant for the model and hence for its interpretation. Three applications of the new descriptor are presented, each representing a different area of 3D-QSAR. For reasons of comparability, the new descriptor was tested on the steroid "benchmark" data set. Furthermore, a highly diverse data set with potentially eye-irritating compounds was studied, and third, a set of flexible structures with a modulating effect on the muscarinic M(2) receptor were studied. Not only were all models highly predictive but interpretation of the back-projected variables into the original molecular space led to biologically and chemically relevant conclusions.
Acetates↗
Accumulation and clearance of capsanthin in blood plasma after the ingestion of paprika juice in men.
The pharmacokinetics of dietary capsanthin was measured in four male volunteers to assess the bioavailability of oxygenated carotenoids (xanthophylls). Capsanthin was used because this carotenoid was not detected in the men's plasma before ingestion of paprika juice. Supplementing capsanthin-rich paprika juice for 1 wk (equivalent to three doses of 5.4 micromol capsanthin/d; 16.2 micromol/d), the level of capsanthin reached a plateau (0.10-0.12 micromol/L) between d 2 and 7 and was not detectable by d 16. Capsanthin was distributed in the plasma lipoproteins (VLDL, 13 +/- 3%; LDL , 44 +/- 3%; HDL, 43 +/- 3%) at the end of the experiment. In a separate experiment involving the single ingestion of paprika juice (equivalent to 34.2 micromol capsanthin) in the same men, the plasma concentration of capsanthin ranged from 0.10 to 0.29 micromol/L at 8 h after ingestion. In contrast, the elevation of the plasma concentration of an acyclic hydrocarbon carotenoid, lycopene, by a single ingestion of tomato soup (equivalent to 186.3 micromol lycopene) in the same subjects was minimal (0.02-0.06 micromol/L). The areas under the curves (AUC) for capsanthin between 0 and 74 h and for lycopene between 0 and 72 h were 4.68 +/- 1.22 and 0.81 +/- 0.17(micromol.h)/L, respectively. The half-lives (t1/2) were calculated to be 20.1 +/- 1.3 and 222 +/- 15 h for capsanthin and lycopene, respectively. We conclude that the clearance of capsanthin is much faster than that of lycopene, although capsanthin is transported into plasma lipoproteins in larger amounts. This polar carotenoid may be metabolized in the human body more rapidly than lycopene. These data justify further research on the physiological functions of capsanthin and other xanthophylls.
Adult↗
Molecular structure and enzymatic function of lycopene cyclase from the cyanobacterium Synechococcus sp strain PCC7942.
A gene encoding the enzyme lycopene cyclase in the cyanobacterium Synechococcus sp strain PCC7942 was mapped by genetic complementation, cloned, and sequenced. This gene, which we have named crtL, was expressed in strains of Escherichia coli that were genetically engineered to accumulate the carotenoid precursors lycopene, neurosporene, and zeta-carotene. The crtL gene product converts the acyclic hydrocarbon lycopene into the bicyclic beta-carotene, an essential component of the photosynthetic apparatus in oxygen-evolving organisms and a source of vitamin A in human and animal nutrition. The enzyme also converts neurosporene to the monocyclic beta-zeacarotene but does not cyclize zeta-carotene, indicating that desaturation of the 7-8 or 7'-8' carbon-carbon bond is required for cyclization. The bleaching herbicide 2-(4-methylphenoxy)triethylamine hydrochloride (MPTA) effectively inhibits both cyclization reactions. A mutation that confers resistance to MPTA in Synechococcus sp PCC7942 was identified as a point mutation in the promoter region of crtL. The deduced amino acid sequence of lycopene cyclase specifies a polypeptide of 411 amino acids with a molecular weight of 46,125 and a pI of 6.0. An amino acid sequence motif indicative of FAD utilization is located at the N terminus of the polypeptide. DNA gel blot hybridization analysis indicated a single copy of crtL in Synechococcus sp PCC7942. Other than the FAD binding motif, the predicted amino acid sequence of the cyanobacterial lycopene cyclase bears little resemblance to the two known lycopene cyclase enzymes from nonphotosynthetic bacteria. Preliminary results from DNA gel blot hybridization experiments suggest that, like two earlier genes in the pathway, the Synechococcus gene encoding lycopene cyclase is homologous to plant and algal genes encoding this enzyme.
Amino Acid Sequence↗