Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Decanoic Acids”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 19 recordsLinked to original sources
PubMed2004

Solid-liquid phase behavior of binary fatty acid mixtures 3. Mixtures of oleic acid with capric acid (decanoic acid) and caprylic acid (octanoic acid).

Solid-liquid phase behavior of binary mixtures of oleic acid (OA)/capric acid (C10A) and OA/caprylic acid (C8A) were investigated by means of differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FT-IR), and X-ray diffraction. The phase diagram of OA/C10A mixture constructed from the DSC results suggested that a molecular compound with the composition of OA:C10A = 3:2 is formed in a solid phase, and OA and the molecular compound are miscible, while C10A and the molecular compound are completely immiscible. The formation of the molecular compound was supported by the IR spectroscopic observation, and a possible model of the structure was proposed on the basis of X-ray diffraction spectrum in small angle region. This compound formation is characteristic of the OA/C10A mixture, and may be attributed to the similarity of the acyl chain length of C10A to the lengths of Delta- and omega-chains of OA (i.e., the chain segments divided by cis-double bond). The mixture of OA and C8A, whose chain length is close to but shorter than the two chain segments of OA, provided a eutectic-type phase diagram showing a partial mixing of the two components in OA-rich region. Thermodynamic analysis of the liquidus line in the phase diagram exhibits a systematic trend for the non-ideality parameter of mixing with the variation of the chain length difference between OA and saturated fatty acid species.

Calorimetry, Differential Scanning↗
PubMed1996

Alteration in membrane fluidity and lipid composition, and modulation of H(+)-ATPase activity in Saccharomyces cerevisiae caused by decanoic acid.

Decanoic acid, a lipophilic agent, inhibited in vitro the plasma membrane H(+)-ATPase of Saccharomyces cerevisiae grown in YPD medium. Conversely, when decanoic acid (35 microM) was present in the growth medium, the measured H(+)-ATPase activity was four times higher than that of control cells. Km, and pH and orthovanadate sensitivity were the same for the two growth conditions, which indicated that H(+)-ATPase activation was not due to conformational changes in the enzyme. The activation process was not entirely reversible which showed that plasma membrane H(+)-ATPase activation is due to several mechanisms. 1,6-diphenyl-1,3,5-hexatriene anisotropy performed on protoplasts from cells grown in YPD revealed that as decanoic acid concentration was increased, anisotropy significantly decreased, i.e. membrance fluidity increased. Cells grown in media containing decanoic acid exhibited greater membrane fluidity compared with control cells. Furthermore, these cells did not show any fluidifying effect when increased concentrations of decanoic acid were added. Chemical analysis of cell membrane lipid composition revealed a modification in the distribution of the phospholipid fatty acids and sterols in cells grown in the presence of 35 microM decanoic acid compared with control cells. Our results support the view that the plasma membrane H(+)-ATPase activation induced by decanoic acid is correlated with an alteration in membrane lipid constituents.

Cell Membrane↗
PubMed1997

Effects of low temperatures (9-33 degrees C) and pH (3.3-5.7) in the loss of Saccharomyces cerevisiae viability by combining lethal concentrations of ethanol with octanoic and decanoic acids.

Octanoic and decanoic acids increase the rate of loss of Saccharomyces cerevisiae viability caused by lethal concentrations of ethanol, the specific death rate being an exponential function of the acid concentration. The highly liposoluble decanoic acid is the most effective. The fatty acids deleterious effect increases at pH below pKa (4.9) mainly due to the increase of the undissociated form concentration. The temperature effects (range 9 33 degrees C; at pH 3.9) on the kinetics of the toxin(s)-induced death suggest that the deleterious action of ethanol, octanoic acid and decanoic acid have the same biological target sites, probably related to transport processes across membranes, particularly the plasma membrane. In fact, the enthalpies of activation of octanoic acid- and decanoic acid-enhanced-ethanol-induced death were similar and close to the enthalpy of activation of ethanol-induced death. This average value (delta H++ = 11.4 +/- 2.7 kcal/mol) is of the order of magnitude of that of solute transport across plasma membranes. Results clearly suggest the important contribution of octanoic and decanoic acids, combined with ethanol, in the loss of yeast viability at the last steps of industrial ethanolic fermentations, particularly those carried out at low or intermediate temperatures. They also support the combination of lipophilic acids with low pH in food preservation.

Caprylates↗
PubMed1994

Effects of perfluoro-n-octanoic acid, perfluoro-n-decanoic acid, and clofibrate on hepatic phosphorus metabolism in rats and guinea pigs in vivo.

Phosphorus-31 nuclear magnetic resonance (NMR) spectroscopy was used to study the effects of perfluoro-n-octanoic acid (PFOA), perfluoro-n-decanoic acid (PFDA), and clofibrate (CLOF) on liver phosphorus metabolism in rats and guinea pigs in vivo. All three compounds are known to cause peroxisome proliferation in rats but not in guinea pigs. The data indicate that indices related to overall tissue viability (i.e., adenosine triphosphate levels) remain unaffected at the doses and experimental times investigated for all treatments and both species. PFDA-treated rats revealed a marked increase in a liver phosphomonoester resonance compared with corresponding controls (p < or = 0.01); no such effect was observed in guinea pigs. This particular 31P NMR signal was identified as phosphocholine (PCho) and was found to steadily increase in concentration at consecutive days post-PFDA treatment, reaching 6.26 +/- 0.29 mumol/g liver at 5 days. This is fourfold greater than the PCho levels determined in livers from corresponding pair-fed control rats. The elevation in liver PCho is a specific response of PFDA treatment in rats and is not simply related to peroxisome proliferation in general, since neither PFOA nor CLOF produce such an effect. The data suggest a unique effect of PFDA on liver phospholipid metabolism, specifically phosphatidylcholine, which may involve enhanced phospholipid turnover via phosphatidylcholine-specific phospholipase C activity.

Animals↗
PubMed1981

C6--C10-dicarboxylic aciduria in starved, fat-fed and diabetic rats receiving decanoic acid or medium-chain triacylglycerol. An in vivo measure of the rate of beta-oxidation of fatty acids.

Administration of decanoic acid to rats resulted not only in elevated urinary excretions of the C10-dicarboxylic acid (sebacic acid), but also in highly elevated excretions of the beta-oxidation products C8- and C6-dicarboxylic acids (suberic and adipic acids). Activation of the lipid metabolism by starvation, fat-feeding and experimental diabetes increased the excretions of adipic acid and decreased the excretions of sebacic acid, i.e. the rate of oxidation of fatty acids was correlated to the adipic : sebacic acid ratio in urine. Compared with nondiabetic unstarved rats the adipic : sebacic acid ratio was elevated 2--3-, 8--16-, 5--19-, and 22--88-times in rats which were, respectively, starved for 2 days, 4 days, on a fat-diet for 4 days, and ketotic due to streptozotocin-induced diabetes. All rats with ratios above 10 were ketotic (urinary excretions of 3-hydroxybutyric acid over 500 microgram/mg creatinine) and all rats with ratios below 4 were nonketotic, while ketosis was a variable finding in rats with intermediary ratios. Similar changes in the ratio of excreted dicarboxylic acids were found when medium-chain triacylglycerols were fed instead of decanoic acid.

Acidosis↗
PubMed1986

Role of octanoic and decanoic acids in the control of seizures.

Octanoic and decanoic acid, the major constituents of the Medium Chain Triglyceride (MCT) Emulsion diet, have been detected in appreciable quantities in the peripheral blood of children with intractable seizures treated with the MCT diet. Serum concentrations of these acids as well as beta hydroxybutyrate and acetoacetate rose as the diet was introduced and on full diet showed pronounced diurnal variation and low concentrations in the morning. No correlation between octanoic and decanoic acid concentrations and control of seizures was established, but further studies with octanoic and decanoic acid using animal models are necessary to assess the role of these acids and of control of seizures.

3-Hydroxybutyric Acid↗
PubMed1988

Relative fluorescence of normal and acid lipase-deficient cultured fibroblasts following administration of pyrene decanoic acid.

Skin fibroblasts, derived from normal individuals or patients with Wolman's disease (an autosomal recessive disorder due to acid lysosomal lipase deficiency) were incubated with the fluorescent fatty acid, pyrene-decanoic acid (P10). Measurements of the fluorescence intensities of the total lipid extracts indicated that equal quantities of P10 were incorporated into both cell types. The fluorescence emitted by the intact cells was subsequently recorded in a fluorescence microscope equipped with a microdetector unit, which permitted determination of the fluorescence emitted by the intact cell or by specific regions thereof. The fluorescence intensities emitted by the lipidotic cells exceeded those of their normal counterparts 2- and 5-fold when comparing the entire cells or the perinuclear region, respectively. The cells were then subjected to subcellular fractionation and an analysis of the fractions revealed that up to 85-90% of the fluorescence of the lysosome-mitochondrial pellet was derived from free pyrenedecanoic acid; the latter contributed only 15-18% to the fluorescence of the homogenate or the cytosol. There was no difference in the fluorescence of the lipid extracts from the respective fractions of the lipidotic or normal cells. However, the fluorescence emitted by the intact lysosome-mitochondrial fraction of the lipidotic cells exceeded that of its normal counterpart 2.5-fold. These data suggest that the increased fluorescence intensity of the intact lipidotic cells resulted from a higher quantum yield of free P10 molecules solubilized in the hydrophobic environment of their neutral lipid-containing storage granules.

Cell Compartmentation↗
PubMed1985

Influence of the diet on the portal and lymph transport of decanoic acid in rats. Simultaneous study of its mucosal catabolism.

The absorption route of decanoic acid, a medium chain fatty acid, infused in the intestinal lumen in the presence and absence of long chain fatty acids, has been analyzed. Ex vivo perfusion of isolated intestinal loop and intestinal lymph fistula was the technique used. Decanoic acid infused alone was essentially transported through the portal system. If infused in association with monopalmitin, oleic or palmitic acid, up to 3% of decanoic acid could be diluted in the lymph. Moreover, decanoic acid oxidation by the mucosa increased significantly with palmitic acid and in contrast decreased with oleic acid. These data show that both intestinal absorption processes and mucosal oxidation of the medium chain fatty acids are modulated by the lipid components of the diet.

Animals↗
PubMed1987

The effects of perfluoro-n-decanoic acid (PFDA) on rat heart beta-receptors, adenylate cyclase, and fatty acid composition.

Perfluoro-n-decanoic acid (PFDA) is a member of a family of surfactants with numerous industrial applications. The acute toxicity of PFDA is characterized by body wasting and delayed lethality. Recent reports have indicated that the effects of PFDA may involve an action on the structure of biological membranes which results in an alteration of function. In the present study we extend our work on the membrane actions of PFDA by examining its effects on myocardial beta-adrenoceptor binding characteristics and adenylate cyclase. Following a single injection of PFDA the apparent number of beta-receptor binding sites was reduced compared to pair-fed controls. This change in beta-receptor binding capacity was reflected in a reduced ability of norepinephrine to activate adenylate cyclase. No alterations were observed in basal adenylate cyclase activity or in the ability of NaF or guanylyl imidodiphosphate to stimulate the enzyme. The fatty acid composition of the heart was changed by PFDA treatment. Our results suggest that the toxic effects of PFDA may be due to an alteration of the membrane lipid bilayer leading to changes in the functional activity of myocardial membranes.

Adenylyl Cyclases↗
PubMed1995

Intestinal absorption and lymphatic transport of eicosapentaenoic (EPA), docosahexaenoic (DHA), and decanoic acids: dependence on intramolecular triacylglycerol structure.

We compared the absorption of eicosapentaenoic (EPA, 20:5n-3), docosahexaenoic (DHA, 22:6n-3), and decanoic acids in mesenteric lymph duct-cannulated rats following intragastric administration of two oils with different intramolecular triacylglycerol structures. One oil had a specific triacylglycerol structure with EPA and DHA located in the sn-2 position and decanoic acid in the sn-1 and sn-3 positions (specific M-n3-M) whereas the other oil had a random fatty acid distribution (random M-n3-M). The mol% (mol/100 mol total fatty acids) of fatty acids in the two oils was similar, with approximately 66 mol% of decanoic acid and 22 mol% of EPA and DHA. The lymphatic transport (microgram/min) of EPA and DHA as well as the mol% in the total lymph lipids were significantly (both P < 0.01) increased following intragastric administration of specific M-n3-M compared with random M-n3-M. The mol% of decanoic acid in the total lymph lipids was significantly (P < 0.01) higher after random M-n3-M compared with specific M-n3-M but the transport (microgram/min) of decanoic acid was not significantly different. We conclude that under our experimental conditions specific M-n3-M with EPA and DHA predominantly in the sn-2 position of the triacylglycerols was a more readily absorbed source of EPA and DHA and in this context should be investigated further for the potential use in clinical nutrition.

Animals↗
PubMed1987

Cytotoxic and cytolytic activity of nonadecafluoro-n-decanoic acid on Acholeplasma laidlawii.

We studied the interactions between the perfluorinated fatty acid nonadecafluoro-n-decanoic acid (NDFDA) and the cell wall-less procaryote Acholeplasma laidlawii, which were cultured in an identical medium base but with different serum supplements. When grown in mycoplasma media supplemented with PPLO serum fraction (Difco Laboratories, Detroit, Mich.), A. laidlawii was rapidly killed by low concentrations of toxicant (less than 1.0 mM). At higher concentrations (greater than 10 mM), NDFDA treatment appeared to lyse cells. A. laidlawii cells grown in horse serum-supplemented mycoplasma media were both killed and lysed at the same NDFDA concentration (greater than 10 mM). These data suggest that this perfluorinated fatty acid can be cytotoxic and cytolytic to mycoplasmas. Changes in active concentrations occurred in parallel with changes in growth medium serum supplementation, which is known to alter mycoplasma membrane composition. We propose that NDFDA interacts with the membranes of A. laidlawii cells, resulting in cell death or cell lysis or both.

Acholeplasma laidlawii↗
PubMedDate not supplied

Effect of the peroxisome proliferator perfluoro-n-decanoic acid on glucose transport in the isolated perfused rat liver.

The perfluorinated carboxylic acid, perfluoro-n-decanoic acid (PFDA), is a known peroxisome proliferator which displays toxicity in rodents. Using a paired-tracer first-pass extraction technique, the effect of PFDA on hepatic glucose transport was determined in the isolated perfused rat liver. In brief, livers isolated from PFDA-treated and control rats on day 5 posttreatment were administered the radiolabeled glucose analog, 3-O-[14C]methyl-D-glucose ([14C]3-O-MG) in addition to [fructose-1-3H(N)]sucrose ([3H]sucrose), which served as a measure of extracellular volume. Hepatic glucose transport was calculated from the change in the ratio [14C]3-O-MG/[3H]sucrose during passage through the liver. Data from this study indicate that PFDA inhibits hepatic glucose transport. Percent hepatic glucose extraction is 1.8-fold greater in controls than in PFDA-treated rats. No significant difference in lactate dehydrogenase levels was observed in the liver perfusate from PFDA-treated and control rats. This suggests that the difference in percent glucose extraction between PFDA-treated and control groups is specifically due to the PFDA treatment and is not attributed to differences in liver viability between groups. Although the exact mechanism for this inhibition in hepatic glucose transport is not known, it is hypothesized that PFDA may have a major impact on membrane structure/function which, in turn, may alter glucose transport.

Animals↗
PubMed1982

Monitoring octanoic and decanoic acids in plasma from children with intractable epilepsy treated with medium-chain triglyceride diet.

We describe a procedure for gas-chromatographic determination of n-octanoic and n-decanoic acids in 100 microL of plasma from children with intractable epilepsy treated with medium-chain triglyceride (MCT) diet. With n-nonanoic acid as the internal standard, the extraction efficiencies for octanoic and decanoic acids were 98 and 105%, respectively. Within-run CVs for octanoic acid at 0.5, 1.0, 2.5, 5.0, 7.5, and 10.0 micrograms/0.1 mL were 8.8, 7.9, 8.5, 6.5, 4.3, and 5.7%, respectively. For decanoic acid at identical concentrations, the CVs were 10.0, 7.4, 4.9, 4.0, 2.6, and 3.5%, respectively. For 10 children on MCT diet (45.9% of calories supplied as MCT) the mean concentrations of octanoic and decanoic acids were 44.2 and 27.0 mg/L, respectively. Presence of relatively "high" quantities of these acids in plasma may contribute to seizure control when MCT diet is prescribed for intractable childhood epilepsy.

Caprylates↗
PubMed1986

Toxic effects of nonadecafluoro-n-decanoic acid in rats.

Nonadecafluoro-n-decanoic acid (ND-FDA) has a single dose ip LD50 of 41 mg/kg and causes anorexia and a wasting syndrome. NDFDA also appears to affect lipid metabolism although the metabolic fate and mechanism of action are not known. Control rats were pair fed with rats given 50 mg/kg. Body weights and food consumption were measured daily; body and organ weights, tissue histopathology, and hematological and clinical chemistry parameters were determined at 4, 8, 12, 16, and 30 days postdosing. Liver samples were obtained for determining cholesterol, cholesterol esters, phospholipids, total lipids, fatty acid ratios, and NDFDA. The rats became anorectic within 4 days and did not resume feeding for 10-12 days, losing about 40% of their body weight. There was a decrease in serum protein; total liver protein decreased and there was an increase in measured fatty acids except for stearic. Liver to body weight ratios of dosed rats were twice those of control rats since absolute liver weights in dosed rats remained constant during the weight loss period. The most striking histopathological change was seen in the liver with a uniform persistent cellular swelling at all times. Separation of the lipids by thin layer chromatography indicated that NDFDA was present in the most polar fraction. There also were fatty changes in the proximal tubular epithelium of the kidneys.

Animals↗
PubMed1989

HPLC analysis of brain and plasma for octanoic and decanoic acids.

Two methods are described for determination of octanoic and decanoic acids in plasma and brain homogenate by "high-performance" liquid chromatography with ultraviolet detection. Analysis of the underivatized acids had a detection limit of only 50 mg/L, but formation of the p-bromophenacyl ester increased the sensitivity by 100-fold, to a detection limit of 0.5 mg/L. The latter procedure gave interassay coefficients of variation of 4.1% and 4.8% for octanoic and decanoic acids, respectively. The corresponding intra-assay values were 3.95% and 4.7% (n = 6). The derivative method, applied to samples of plasma from children receiving a medium-chain triglyceride (MCT) diet, gave values in agreement with results by gas-liquid chromatography. Results have also been obtained for samples from mice, either treated with the medium-chain triglyceride diet or given infusions of sodium octanoate.

Adolescent↗
PubMed1995

Bioconversion of methyl ricinoleate to 4-hydroxy-decanoic acid and to gamma-decalactone by yeasts of the genus Candida.

The capacity of several strains of yeasts to do the bioconversion of methyl ricinoleate into gamma-decalactone, was studied in a medium containing this methylic ester of fatty acid as sole carbon source. Amongst the strains which are able to do this bioconversion, two types of behaviour are observed: some of the strains produce gamma-decalactone during all the incubation in bioconversion medium while others produce this aroma compound very quickly and then consume it fast too. The tested strains produce at the same time gamma-decalactone and the corresponding acid form (4-hydroxy-decanoic acid), and this, in variable proportions.

Biomass↗
PubMed1986

The effects of perfluoro-n-decanoic acid in the rat heart.

Perfluoro-n-decanoic acid (PFDA) is a synthetic chemical resembling a 10-carbon fatty acid. Several studies have suggested that the toxic mechanism of PFDA may involve impaired lipid metabolism and/or altered cell membrane function. We examined the possibility that altered cell membrane structure in the heart might lead to changes in the functional activity of the organ. Functional characteristics were determined in the isolated perfused rat heart by measuring the ability of the heart to respond to either sympathetic nerve stimulation or infused norepinephrine. PFDA reduced the intrinsic resting heart rate and the inotropic response to a stimulus with maximal effects occurring 8 days after dosing. In addition, resting heart rate measured in vivo was found to be reduced in PFDA-treated rats 6 to 8 days after dosing. beta-Receptor binding studies conducted 8 days after a single dose of PFDA showed that the maximum binding capacity was reduced by PFDA treatment without significant changes in receptor affinity. It is concluded that the reduction in the inotropic response to catecholamines following PFDA treatment may be explained in part by lower beta-receptor density in the myocardial cell membrane. These effects may be related to the early fall in serum thyroid hormone levels as previously reported.

Animals↗