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Synthesis of hippuric acid in dementia praecox. - CAB …

(1971) Excretion of hippuric acid and m- or p-methylhippuric acid in the urine of persons exposed to vapours of toluene and m- or p-xylene in an exposure chamber and in workshops, with specific reference to repeated exposures.

Ingersoll, A. W., Babcock, S. H. 2003. Hippuric Acid. Organic Syntheses. 40.

For example, using the benzoate clearance test (a measure of the rate at which the body detoxifies benzoate by conjugating it with glycine to form hippuric acid, which is excreted by the kidneys), the rate of clearance in those with liver disease is 50% of that in healthy adults

Hippuric Acid For Synthesis | VWR

Metabolites of toluene The major metabolite, hippuric acid, is eliminated in the urine.

(1982) Determination of urinary hippuric acid and o-cresol, as indices of toluene exposure, by liquid chromatography on dynamically-modified silica.

The biotransformation of toluene to o-cresol and hippuric acid was not affected by n-hexane, as assessed by the urinary concentrations of these toluene metabolites (Takeuchi et al., 1981a; Honma, 1983; Perbellini et al., 1982).

The biological synthesis of hippuric acid in vitro - CORE

The hippuric acid excretion metabolites of toluene are reduced by benzene.

(1970) carried out a study on human volunteers and found that the quantity of hippuric acid excreted was proportional to the total exposure (mg/m3 x h).

(1982), it is concluded that the urinary levels of hippuric acid are proportional to the concentrations of toluene in the air, though within wide variations.

(1971) [The urinary excretion of hippuric acid in workers exposed to toluene.]  Med.
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Although phenylacetic acid has been studied extensively, investigations conducted before 1950 on human metabolism (Shiple & Sherwin, 1922; Power & Sherwin, 1927; Ambrose et al.,1933; Wagreich et al.,1940) failed to account for the endogenous level of 250–500 mg/kg per day of phenylacetic acid conjugated with glutamine (Stein et al., 1954) present in human urine and did not adequately characterize the array of urinary conjugates that were formed from phenylacetic acid. More recent work demonstrates that conjugation is both dose-dependent and species-specific. The major metabolic options available to phenyl acetic acid are conjugation with glucuronic acid, glycine, taurine or glutamine and elimination as the free acid.


In a study of the effects of various phenyl-substituted acids on the activity of glycosyl transferase (used in cerebral glycoprotein synthesis) in human cerebrospinal fluid, a 1-h incubation with phenylacetic acid (2–10 mmol/l) produced up to 91% inhibition (Ko et al., 1973).

The Role of the Liver in Hippuric Acid Synthesis

No increase in sister chromatid exchange frequency was observed when human whole blood lymphocyte cultures were exposed to 2-phenethyl alcohol (No. 987) for 72 h (Norppa & Vainio, 1983). Also, no increase in unscheduled DNA synthesis was noted when rat hepatocytes were incubated with phenylacetic acid (Heck et al., 1989). Incubation of ethyl phenylacetate at 1000 µg/ml with Chinese hamster fibroblasts for 48 h caused chromosomal aberrations in 3% of cells. On the basis of a threshold of positivity of > 10%, ethyl phenylacetate gave negative results in this assay (Ishidate et al., 1984).

Health Consequences of Catabolic Synthesis of Hippuric Acid in Humans

Some 60 - 75% of absorbed toluene is metabolized to benzoic acid by the microsomal mixed-function oxidase system, with subsequent conjugation with glycine to form hippuric acid.

Synthesis of hippuric acid in liver homogenate - CORE

I actually participated in the Urination Derby as an undergrad back in 1975. Our Biochem professor divided the lab into partners. One had to do the biosynthesis by drinking a measured amount of sodium benzoate, collecting urine over the next hours, and isolating the hippurate. The other had to do a chemical synthesis of hippuric acid from glycine and benzoyl chloride. You could tell the students doing the biosynthesis by their pale faces and stoic expressions–the human stomach is not particularly happy with benzoate solutions. The big problem with the experiment was that we were using a Bio Department lab that had only one fume hood. This was used to dispense the benzoyl chloride, which is a potent lachrymator. This meant that over the course of the experiment there were students carrying around open beakers of both urine and benzoyl chloride. The air in the lab got pretty foul!

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