The metabolism of benzyl acetate involves very rapid hydrolysis to acetate and benzyl alcohol. The latter is subsequently mainly oxidized to benzaldehyde and benzoic acid. A small part of the benzyl alcohol may be conjugated with sulfate, leading, ultimately, to formation of a glutathione conjugate that is excreted as mercapturate in urine. The benzoic acid is excreted mainly as hippurate and, to a lesser extent, as acyl glucuronide (see ).
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Benzyl acetate is quite soluble in lipids and therefore readily absorbed from the gastrointestinal tract and lung, as well as through the skin, in the species investigated. The absorption after oral administration in the rat was delayed if it was administered in corn oil or propylene glycol as compared to neat [methylene-14C]benzyl acetate (Chidgey & Caldwell, 1986): the peak plasma concentration of benzyl acetate-derived radioactivity occurred later (Tmax after 1 h versus 4–6 h) and was lower at a 500 mg/kg benzyl acetate dose; at 5 mg/kg benzyl acetate, there was no difference. The urinary excretion of the metabolites was also delayed by corn oil, but the extent of absorption seemed not to be affected: more than 80% was absorbed and excreted within 24 h, mainly in urine and, ultimately, less than 5% in faeces. In plasma and urine, no intact benzyl acetate was detected at any time; only its metabolites were present (Chidgey & Caldwell, 1986). Benzyl acetate is rapidly hydrolysed by esterases to benzyl alcohol and acetate (Yuan et al., 1995). These esterases are present in plasma and probably also in the tissues; it is possible that during absorption benzyl acetate is already hydrolysed, so that little if any of the intact compound reaches the general circulation (Hotchkiss et al., 1992). The peak plasma levels of the metabolite benzoic acid in rats and mice fed benzyl acetate in the diet were much lower than after gavage of roughly the same dose, whereas the levels of hippurate were very similar (Yuan et al., 1995). The explanation may be that glycine conjugation of benzoic acid becomes saturated after the high, acute gavage dose, while during feeding the dose is more slowly taken up. Yuan et al. (1995) provide a pharmacokinetic model of benzyl acetate in rats and mice. Extensive absorption after dermal application of 100–500 mg/kg to rats was observed: 35–55% of the dose was recovered as metabolites in urine within 24 h (Chidgey et al., 1987). The metabolic profile was the same as after oral or intravenous administration. Some data on organ distribution of radioactivity were provided. This percutaneous absorption was confirmed in vitro with rat and human skin (Hotchkiss et al., 1990, 1992; Garnett et al., 1994). Dimethylsulfoxide had a minor enhancing effect on skin absorption. The absorption rate through rat skin was approximately six-fold that through human skin. The identity of the absorbed radioactivity was not determined, but most likely represented benzyl acetate metabolites.
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No unchanged benzyl acetate was detected in rat or mouse plasma. The plasma concentrations of metabolites after intravenous administration of 5 mg/kg bw benzyl acetate (McMahon et al., 1989) showed only minor changes with age (3–4, 9 and 25 months) in Fischer 344 rats and B6C3F1 or C57BL/6N mice. In urine, by far the major metabolite is the hippurate at all doses and in all species (Abdo et al., 1985; Chidgey & Caldwell, 1986; McMahon et al., 1989). The acyl glucuronide of benzoic acid comprised from 2 to 12% of the urinary metabolites (low versus high dose) and benzyl mercapturate 1–2% of the dose (Chidgey & Caldwell, 1986). This mercapturate is probably formed from benzyl alcohol through its (reactive) sulfate ester, since prevention of oxidation by pyrazole increases the mercapturate from 1.1 to 12% of the dose, while the sulfation inhibitor pentachlorophenol subsequently decreases it again to 2% (Chidgey et al., 1986).
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