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PubMed2003

High performance liquid chromatographic determination of acetoacetate by post-column derivatization with p-nitrobenzene diazonium fluoroborate.

We have applied a color-developing reagent, p-nitrobenzene diazonium fluoroborate (diazo reagent) as a post-column derivatization tool for the specific determination of acetoacetate (AcAc) in high performance liquid chromatography (HPLC). A mobile phase consisting of 50 mM KH(2)PO(4), 4 mM tetra-n-butylammonium phosphate (TBAP) as an ion-pair reagent and 2 v/v% methanol, pH 3.5, diazo reagent solution with 0.2% triton X-100, and alkaline solution of 1.5 mol/l NaOH were pumped using three independent pumps. Specific color development on-line was monitored at 645 nm. A calibration curve for AcAc standard solution with an injection volume of 20 microl showed a good linearity in the range 0.01-2.5 mM with a correlation coefficient of 0.999. For the determination of 3-hydroxybutyrate (3-HOBA), 3-HOBA was converted to AcAc by an enzymatic-coupling method using 3-HOBA dehydrogenase and lactate dehydrogenase. Analytical recoveries of AcAc and 3-HOBA added to serum and urine were satisfactory.

Acetoacetates↗
PubMed1997

NADPH-dependent reduction of ethyl acetoacetate coupled with ethanol oxidation in Kloeckera magna.

We evaluated the catalytic ability of 29 yeast strains to reduce ethyl acetoacetate (EA) in the presence of ethanol or glucose. In 18 yeast strains, the reduction in the presence of ethanol proceeded as well as in the presence of glucose. Among them, Kloeckera magna (AKU 4704) effectively catalyzed the NADPH-dependent reduction of EA in the presence of ethanol. In this reduction, 1 mol of EA was reduced by consuming 1 mol of ethanol. We found that the NADPH regeneration system responsible for EA reduction in K. magna was coupled with oxidation of acetaldehyde to acetic acid catalyzed by an NADP(+)-dependent aldehyde dehydrogenase.

Acetoacetates↗
PubMed1988

Blood glucose, lactate, pyruvate, glycerol, 3-hydroxybutyrate and acetoacetate measurements in man using a centrifugal analyser with a fluorimetric attachment.

Methods are described for the analysis of glucose, lactate, pyruvate, alanine, glycerol, 3-hydroxybutyrate and acetoacetate in perchloric acid extracts of human blood, using the Cobas Bio centrifugal analyser fitted with a fluorimetric attachment. Intra-assay and inter-assay coefficients of variation ranged from 1.9 to 7.9% and from 1.0 to 7.2% respectively. Correlation coefficients ranged from 0.96 to 0.99 against established continuous-flow and manual spectrophotometric methods. All seven metabolites can be measured using a single perchloric acid extract of 20 microliter of blood. The versatility of the assays is such that as little as 100 pmol pyruvate, 3-hydroxybutyrate or as much as 15 nmol glucose can be measured in the same 20 microliter extract.

Acetoacetates↗
PubMed1992

Spectral evidence for the oxidation of beta-hydroxybutyrate to acetoacetate: diminution of spectra by glucose and chloride.

Chemical oxidation of beta-hydroxybutyrate (beta-OHB) to acetoacetate (AcAc) has been carried out by a simple and new method employing potassium persulphate as an oxidising agent. Under the conditions of assay, beta-OHB (0.079-0.395 microM) was instantaneously oxidised to AcAc and the authenticity of the oxidised product was proved by absorption spectroscopy. A common absorption maxima at about 446 nm was observed in all the spectra recorded for the product (AcAc-complex) obtained after the oxidation of beta-OHB (0.079-0.395 microM) to AcAc followed by coupling with diazotized p-nitroaniline. This absorption maxima was almost equal to that obtained for AcAc-complex using AcAc as reference standard. It implies that AcAc formed by the chemical oxidation of beta-OHB is identically similar to the AcAc used as reference standard for the study. This fact was further strengthened when absorption spectra, recorded either individually or in combination (mixed-type), exhibited a single peak with a common absorption maxima at about 446 nm. Absorption spectra was found to be partially diminished by glucose (1.77 microM) and chloride (17.1 microM), while almost complete diminution of absorption spectra was observed at higher concentration of glucose (8.88 microM) and chloride (51.3 microM).

3-Hydroxybutyric Acid↗
PubMed1990

Ketosis treatment and milk yield in dairy cows related to milk acetoacetate levels.

Milk yield and milk acetoacetate (M-acac) were measured weekly for the first 6 weeks of lactation in 5 herds with a ketosis problem. Ketosis treatments and the corresponding ketotest score, were also recorded. The treatment rate was highest 7-16 days after calving. Most of these early cases were associated with low ketone levels in milk, whereas the treatment rate for cows with high ketone levels was highest 17-31 days after calving. Nearly half of the treated cows were low-ketone animals. They were classified as ketosis cases in the cow health card records, although probably suffering from other post partum disturbances in many instances. About 40% of the cows with high ketone levels recovered spontaneously. Reduction in milk yield associated with peak M-acac levels was transient and moderate. It was concluded that health card statistics overestimates the severity of the ketosis problem in Norway.

Acetoacetates↗
PubMedDate not supplied

[Reaction of glycine with acetoacetate and various properties of the catalyzing enzyme from the rat liver].

The enzymic interaction between acetoacetate and glycine which are added outside is established to occur in the tissue homogenates of the liver, kidneys and spleen of rats. The interaction leads to a decrease of the both components in the equivalent quantities. Homogeneous crystalline preparations of the enzyme catalyzing the above mentioned reaction are isolated from the liver tissues and purified. Certain properties of the enzyme are studied.

Acetoacetates↗
PubMed1989

Multipoint kinetic method for simultaneously measuring the combined concentrations of acetoacetate-beta-hydroxybutyrate and lactate-pyruvate.

This is a multipoint kinetic method for simultaneously determining acetoacetate (AcAc) plus beta-hydroxybutyrate and lactate plus pyruvate in a single cuvette of the Multistat III centrifugal analyzer. In the first step, AcAc and pyruvate are completely reduced, using 3-hydroxybutyrate dehydrogenase (EC 1.1.1.30) and lactate dehydrogenase (EC 1.1.1.27) in the presence of excess NADH at pH 7.5, to beta-hydroxybutyrate and lactate, respectively. After dilution, the endogenous beta-hydroxybutyrate and lactate and that resulting from reduction are simultaneously oxidized by their respective dehydrogenases in the presence of excess NAD+ at pH 9.0. Adjustment of the relative enzyme concentrations allows simultaneous estimation of AcAc plus beta-hydroxybutyrate and lactate plus pyruvate by analyzing multipoint absorbance data, collected during the oxidation reaction, with use of a two-component linear-regression model. Total run-to-run CVs were 6.4% and 6.1% at 5 mmol/L beta-hydroxybutyrate and 5 mmol/L lactate, respectively. The method was designed to be useful for identifying the cause of an increased anion gap in serum.

3-Hydroxybutyric Acid↗
PubMed1987

Contribution of whole blood L-lactate, pyruvate, D-lactate, acetoacetate, and 3-hydroxybutyrate concentrations to the plasma anion gap in horses with intestinal disorders.

Increased anion gap (AG) was due, in part, to L-lactic acidosis in 14 of 14 horses with intestinal disorders. In a few horses, increased whole blood concentrations of D-lactate made a minor contribution to the AG. However, the increase in AG was often greater than the sum of the increases in these 2 acid anions. This unexplained increase was not a result of increases in whole blood pyruvate, 3-hydroxybutyrate, or acetoacetate concentrations or serum albumin or phosphate concentrations. Identification of other anions causing increased AG could lead to better understanding, diagnosis, and treatment of metabolic imbalances in critically ill horses.

3-Hydroxybutyric Acid↗
PubMed1978

Pyrrolnitrin analogues. V. Knorr's pyrrole condensation between N-(4-nitrophenacyl)-3,5-dimethylaniline and ethyl acetoacetate.

The reaction between N-(4-nitrophenacyl)-3,5-dimethylaniline and ethyl acetoacetate in boiling ethanol afforded 3-carbethoxy-5-(1-carbethoxyacetonyl)-4,5-dihydro-1-(3,5-dimethylphenyl)-4-hydroxy-2-methyl-4-(4-nitrophenyl)pyrrole and in low yield 3-carbethoxy-1-(3,5-dimethylphenyl)-2-methyl-4-(4-nitrophenyl)pyrrole. Chemical transformation of the former compound into 5-acetonyl-1-(3,5-dimethylphenyl)-2-methyl-4-(4-nitrophenyl)pyrrole is described. The structure of 3-carbethoxy-5-(1-carbethoxyacetonyl)-4,5-dihydro-1-(3,5-dimethylphenyl)-4-hydroxy-2-methyl-4-(4-nitrophenyl)pyrrole has been established by the aid of N.M.R. spectral data. The above reaction, when carried out in boiling ethanol in the presence of a catalytic amount of 3,5-dimethylaniline hydrobromide, led to the formation of 3-carbethoxy-1-(3,5-dimethylphenyl)-2-methyl-4-(4-nitrophenyl)pyrrole and 4,6-dimethyl-2-(4-nitrophenyl)indole, the former formed in a very good yield. Some pyrrolnitrin analogues have been prepared starting from 3-carbethoxy-1-(3,5-dimethylphenyl)-2-methyl-4-(4-nitrophenyl)pyrrole.

Acetoacetates↗
PubMed1984

The stimulation of hepatic gluconeogenesis by acetoacetate precursors. A role for the monocarboxylate translocator.

The regulation of the gluconeogenic pathway from the 3-carbon precursors pyruvate, lactate, and alanine was investigated in the isolated perfused rat liver. Using pyruvate (less than 1 mM), lactate, or alanine as the gluconeogenic precursor, infusion of the acetoacetate precursors oleate, acetate, or beta-hydroxybutyrate stimulated the rate of glucose production and, in the case of pyruvate (less than 1 mM), the rate of pyruvate decarboxylation. alpha-Cyanocinnamate, an inhibitor of the monocarboxylate transporter, prevented the stimulation of pyruvate decarboxylation and glucose production due to acetate infusion. With lactate as the gluconeogenic precursor, acetate infusion in the presence of L-carnitine stimulated the rate of gluconeogenesis (100%) and ketogenesis (60%) without altering the tissue acetyl-CoA level usually considered a requisite for the stimulation of gluconeogenesis by fatty acids. Hence, our studies suggest that gluconeogenesis from pyruvate or other substrates which are converted to pyruvate prior to glucose synthesis may be limited or controlled by the rate of entry of pyruvate into the mitochondrial compartment on the monocarboxylate translocator.

3-Hydroxybutyric Acid↗
PubMed1980

Direct, fixed-time kinetic assays for beta-hydroxybutyrate and acetoacetate with a centrifugal analyzer or a computer-backed spectrophotometer.

In the course of studying the control of blood glucose in juvenile onset diabetics, we developed convenient methods for determining beta-hydroxybutyrate and acetoacetate. Here we describe fixed-time, enzymic, reaction-rate procedures for directly measuring these organic acids with a centrifugal analyzer (Rotochem IIA/36) or a computer-backed spectrophotometer (Gilford 102 system). In either case, the method requires only 20 micro L of plasma; is rapid, accurate, and precise; and analytical recovery is quantitative. Data are presented comparing results obtained with both instruments. Metabolic acidosis can be rapidly assessed and monitored with these methods, as illustrated by an example.

Acetoacetates↗
PubMed1982

[Technical study of hydroxybutyrate and acetoacetate levels in blood and milk of cattle].

A method for sampling, for preservation of these samples and for dosage has been studied in order to gain a better knowledge of the usual values and the physiological and pathological variations of beta-hydroxybutyrate and of acetoacetate in the blood and milk of cattle. These methods permit the practical realization of sampling. They also make possible the transportation of these samples, though on the condition that they are immediately frozen or put into refrigeration. The study of the dosage parameters and of their effect has led to a standardization which makes it possible to obtain both a satisfactory yield and satisfactory accuracy.

3-Hydroxybutyric Acid↗
PubMed1994

Prefeeding plasma acetoacetate and glucose in healthy, lactating heifers. Variations related to milk yield, metabolic balances and stage of lactation.

When measured before morning feeding plasma acetoacetate (ACAC) increased and glucose (GL) decreased significantly with increasing milk yield (fat corrected, FCM) within 2 groups of half-sister related heifers which did not suffer from clinical ketosis. The groups received respectively A: 7 kg and B: 4 kg/d of concentrates in addition to grass silage ad libitum (each group 88 animals). Correlation coefficients of the same magnitude between the 3 variables mentioned were obtained in the 1st and 3rd month of lactation in spite of a narrowing of the ACAC range from 0.024-0.66 to 0.019-0.16 mmol/l. Reproducibility of differences between animals in milk yield and in the plasma components was evidenced by significant correlations between measurements in the 1st and 3rd month. The B-animals produced 2.4 kg/d less FCM than the better fed A group (A, 1st month of lactation 19.8 +/- 3.1 kg/d) while the mean values for ACAC and GL remained practically unaffected by the difference in feeding. B cows gave consistently 5-6% lower GL means (p < 0.01) than A animals with identical yields. Animals which showed marked ACAC increment during the first 5-6 weeks of lactation produced 3-4 kg more FCM/d than equally fed animals with constantly low ACAC levels. The estimated energy deficit of this ketonaemic, high-producing category corresponded to the production of 4.5-6 kg FCM/d from body reserves. Low ACAC values (< 0.05 mmol/l) were reproduced with a standard deviation of +/- 4% with the automated nitroprusside method described.

Acetoacetates↗
PubMed1995

Determination of lactate, pyruvate, beta-hydroxybutyrate and acetoacetate with a centrifugal analyser.

Lactate, pyruvate, beta-hydroxybutyrate, and acetoacetate are intermediary metabolites normally occurring in blood. Their relative concentrations are an expression of nutritional balance in energy metabolism. The simultaneous determination of these four analytes is of special interest in the understanding of energy homeostasis. Rapid, precise routine measurement of these four analytes is basic for the first orientation of the diagnosis of inborn errors of intermediary metabolism, especially those affecting fuel homeostasis. We describe an adaptation of the Cobas Fara II centrifugal analyser of some previously reported methods using the supernatant of a unique deproteinized blood sample for the determination of the four analytes. Reference values are calculated for a pediatric population. The difficulties involved in the diagnosis and follow-up of mitochondrial diseases in children require the standardization of analytical procedures for the correct interpretation of the results.

3-Hydroxybutyric Acid↗
PubMed2004

Domino Michael-Aldol reactions on 1,4-diarylbut-2-ene-1,4-diones with methyl acetoacetate furnish methyl 2-aroyl-4- hydroxy-6-oxo-4-arylcyclohexane-1-carboxylate derivatives.

Domino Michael-Aldol reactions on 1,4-diaryl-2-butene-1,4-diones with methyl acetoacetate in the presence of activated Ba(OH)(2) furnished methyl (1R*,2S*,4S*)-2-aroyl-4-hydroxy-6-oxo-4-arylcyclohexane-1-carboxylate derivatives in a stereo- and regiospecific manner. While treatment of these cyclohexanecarboxylate products with TsOH resulted in the dehydrated and decarbomethoxylated cyclohexenone derivatives, the reaction with NaOMe furnished 3,5-disubstituted phenols via dehydration, decarbomethoxylation, and dehydrogenation. NaCl/DMSO under microwave irradiation transformed the cyclohexanecarboxylate products to the 7-hydroxyisobenzofuranone derivatives.

Journal Article↗
PubMed2004

Preparation of beta-keto esters and beta-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles.

Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-l are prepared by reactions of 1-acylbenzotriazoles 1a-k with acetoacetic esters 5 or 7a,b in the presence of sodium hydride followed by regioselective deacetylation. Similar C-acylation/deacetylation of acetylacetone and benzoylacetone affords beta-diketones 10a-d and 13a-c, respectively.

Journal Article↗
PubMed1983

Loss of acetoacetate coenzyme A transferase activity in tumours of peripheral tissues.

The presence of succinyl-coenzyme A: acetoacetate CoA--transferase (3-oxo acid-CoA transferase), an initiator of ketone body utilization in non-hepatic tissue was examined in a number of animal and human tumours of peripheral tissues. While enzyme levels in heart, kidney, lymphocytes and bladder were high, the tumours contained low or non-detectable levels of transferase activity, comparable with that of normal liver. The activities of acetoacetyl-CoA thiolase paralleled that of the transferase, except for the high activity in liver, and in all cases the tumour content of the enzyme was lower than that of the brain. The activity of 3-hydroxybutyrate dehydrogenase was similar in both normal and tumour tissue. The results indicate that tumours of non-hepatic tissues may be unable to metabolize ketone-bodies and suggest a therapeutic strategy for selective starvation of the tumour by dietary modification.

3-Hydroxybutyric Acid↗