Sodium phenylacetate

The production of a-phenylcinnamic acid by heating benzaldehyde with acetic anhydride and sodium phenylacetate ... 

Sodium phenylacetate [114-70-5] M 158.1. Its aqueous solution was evaporated to crystallisation on a steam bath, the crystals being washed with absolute EtOH and dried under vacuum at 80°. 

Urea cycle defects Failure to convert ammonia to urea via urea cycle (Fig. 40-5). Coma, convulsions, vomiting, respiratoryfailure in neonate. Often mistaken for sepsis of the newborn. Mental retardation, failure to thrive, lethargy, ataxia and coma in the older child. Associated with hyperammonemia and abnormalities of blood aminogram Low protein diet Acylation therapy (sodium benzoate, sodium phenylacetate) Arginine therapy in selected syndromes Hepatic transplantation... 

All enteral feeds were stopped. The baby was given intravenous glucose, L-arginine, sodium benzoate, and sodium phenylacetate. Hemodialysis was initiated. At this time, there were no spontaneous respirations, there was no response to painful stimuli, and brainstem reflexes were absent. The plasma amino acid results revealed a glutamine level of 1500 pmol/L (normal 254-823), and citrulline was undetectable (normal 10-34 pmol/L). Quantitative carnitine, plasma acylcarnitine, and urine organic acid profiles were normal. The urine orotic acid concen-... 

A patient with OTC deficiency has recurrent hyperammonemic events over a 3-month period despite reduced protein intake and increased doses of sodium benzoate and sodium phenylacetate. What are the factors that need to be considered as a cause of the hyperammonemia in this individual (Consider the dynamic of nitrogen balance over this period.) What is the likely treatment ... 

In the Pschorr synthesis (Scheme 12.12), a Perkin reaction (see Chapter 6) between 2-nitrobenzaldehyde and sodium phenylacetate in the presence of acetic anhydride yields 3-(2-nitrophenyl)-2-phenyl-propenoic acid. Reduction of the nitro group and deamination of the resulting amine via its diazonium salt (see Chapter 8) is accompanied by cyclization. Thermal decarboxylation completes the sequence. 

A review of the literature of this reaction to 1941 has been made. The condensation is most valuable for the preparation of substituted cinnamic acids, particularly those containing halo, methyl, and nitro groups. Furfural has been condensed in good yields with acetic anhydride, butyric anhydride, and sodium phenylacetate in the... 

Sodium benzoate Sodium benzoate has already been successfully used to treat congenital enzymatic defects of the urea synthesis (M. L. Batshaw et at, 1981). In HE, the administration of sodium benzoate or sodium phenylacetate (each 10 g/day) achieved clinical success equivalent to lactulose therapy in ca. 80% of cases. (122, 144, 159) These substances (which are cheap and practically free of side effects) lead to an increased excretion of nitrogen through the conjugation of glycine and glutamine, whereby ammonium is bound as hippuric acid and excreted renally (bypassing the urea cycle). 

Del Rosario, M., Werlin, S.L., Lauer, S.J. Hyperammonemic encephalopathy after chemotherapy. Survival after treatment with sodium benzoate and sodium phenylacetate. X. Clin. Gastroenterol 1997 25 682- 684... 

Treatment involves a low-protein diet (0.5-0.7 g/kg BW/day) with a sufficient supply of calories. Substitution of essential amino acids (in about the same quantity) is required. The administration of benzoate (0.1-0.25 g/kg BW/day), arginine hydrochloride (1 mmol/kg BW/day) or sodium phenylacetate (0.3-0.5 g/ kg BW/day) (phenylbutyrate tends to be more effective) facilitates nitrogen excretion via other metabolic pathways. (168-170) With an enhanced excretion of orotate or other metabolites of pyrimidine synthesis, the administration of allopurinol leads to an increase in the excretion of nitrogen via metabolites from pyrimidine synthesis. Ammonia and urea precursors are eliminated by haemodialysis. In individual cases, liver transplantation is indicated. (I7l)... 

Thiele and Schleussner prepared ira/ii,franj-l,4-diphenylbutadiene by reaction of cinnamaldehyde with sodium phenylacetate and acetic anhydride at a temperature such that the initially formed product of Perkin condensation loses carbon dioxide. Kuhn and Winterstein employed lead oxide as the base and reported an increase in crude yield from 20 to 34%. The lower yield of 23-25% reported in Organic... 

Sodium benzoate sodium phenylacetate (25 mg/kg p.o. daily) is used as an adjunctive therapy for the prevention of hyperammonemia in patients with urea cycle enzymopathy. 

Although acetic anhydride is often used in the Perkin reaction as the acid anhydride component, other acid anhydrides can be used in the Perkin reaction as well. Oglialoro reported that sodium phenylacetate 21 and acetic anhydride give a-phenylcinnamic acid 22. The Oglialoro modification generates a mixed anhydride in situ and is a convenient preparative method that obviates the necessity of using the arylacetic anhydride as a starting material.2... 

A), a "chemical biopsy" can be performed on animals or on human beings, who may ingest gram quantities of sodium phenylacetate without harm. The phenylacetate is converted to an amide with glutamine (phenylacetylglutamine) which is excreted in the urine, from which it can easily be recovered for analysis. "" This provides a non-invasive way of studying the operation of the citric acid cycle in the human body. Direct measurement on animal brains°T and on human limbs or brain has also been accomplished by NMR spectroscopy ) and may become more routine as instrumentation is improved. ... 

Prasaana, P., Thibault, A., Liu, L. Sami D. (19%). J. Neurochem. 66 710-716. Lipid metabolism as a target for brain cancer therapy Synergistic activity of lovastatin and sodium phenylacetate against human gliomas. 

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