(v) 4-Phenyl-3-buten-2-one (No. 820)
(f) Special studies: 1-Phenyl-1-propanol (No. 822)
1-4-trifluoromethylphenyl-1-2-propandione | VWR
Dix, K.J., Grizzle, T.B., Handy, R.W., Brine, D.R. & Collins, B.J. (1997a) Toxicokinetics of benzophenone (BPH) in male and female rats and mice. , 36 (Part 2), 141.
When rats were given a single intraperitoneal dose of racemic, labelled [3H-C1]-methylbenzyl alcohol, the urinary mandelic acid was chiral ((–)form) but did not contain the 3H label, suggesting that the alcohol was oxidized (dehydrogenated) to acetophenone before formation of mandelic acid. Acetophenone thus appears to be the precursor of optically active mandelic acid, given that either stereoisomer or the racemic form of -methylbenzyl alcohol forms only the (–) form of mandelic acid. Formation of benzoic acid from acetophenone was confirmed when groups of eight male rats exhaled 30% of a single dose of 100 mg/kg bw of [methyl-14C]acetophenone as 14CO2 within 30 h. The intermediate role of -hydroxyaceto-phenone in the formation of benzoic acid and mandelic acid is indicated by the observation that incubation of acetophenone with rat hepatocyte microsomes yields mainly -hydroxyacetophenone (Sullivan et al., 1976).
1-phenyl-3-(2-thenoyl)-1,3-propanedione, Hbth, pKa' ..
Metabolic interconversion of 1-phenyl-1-propanol (No. 822) and propiophenone (No. 824) has been observed . Metabolic reduction of propiophenone produced 19% and 24% 1-phenyl-1-propanol in NADPH- and NADH-fortified male rat liver preparations, respectively. Male rabbit liver homogenate incubated with propiophenone and fortified with NADPH- and NADH-generating systems produced 75% and 61% 1-phenyl-1-propanol, respectively. Other minor metabolic pathways detected included hydroxylation of the -methylene group to produce 2-hydroxy-propiophenone and oxidation of 1-phenyl-1-propanol or propiophenone to yield acetophenone (4–8%). A larger amount of propiophenone (17–18%) was produced in both rat liver preparations (Coutts et al., 1981). In a follow-up experiment, 93–97% of the 1-phenyl-1-propanol produced from propiophenone in rat and rabbit preparations occurred as the (–)-isomer. The remainder occurred in the (+) form. NADPH- and NADH-generating systems were equally efficient in the two species (Prelusky et al., 1982).
The mode of administration and the species have little effect on the metabolic fate of the alcohol or ketone. The major urinary metabolites were still the glucuronic acid conjugate of -methylbenzyl alcohol (35%) and hippuric acid (24%) when rabbits were given a single subcutaneous dose of acetophenone at 500–1400 mg/kg bw. Small amounts were excreted as mandelic acid or unchanged (Thierfelder & Daiber, 1923). When dogs were given a single oral dose of 500 mg/kg bw, 35% was recovered in the urine as the glucuronic acid conjugate of -methylbenzyl alcohol, while 20% was excreted as hippuric acid. Much of the remainder was excreted unchanged (Quick, 1928).
The presence of ,-unsaturation in -4-phenyl-3-buten-2-one does not significantly alter the metabolic fate of this ketone when compared with that of other aromatic ketones. The glycine conjugate of phenylacetic acid, phenaceturic acid (65%), was the major urinary metabolite collected 48 h after male Fischer 344 rats were given a single dose of 200 mg kg bw -4-phenyl-3-buten-2-one (No. 820) by oral gavage. Minor urinary metabolites included hippuric acid (9.9%) and glutathione conjugates of the parent ketone (5.6%) and alcohol (2.2%). Presumably, hippuric acid (benzoylglycine) is formed from hydration of the double bond, subsequent retro-aldol reaction to form benzaldehyde, and then oxidation to benzoic acid. The parent ketone was not detected in blood after dosing. The principal blood metabolite after intravenous administration of the same dose was the corresponding alcohol, 4-phenyl-3-butene-2-ol, which represented 4.4% of the total dose. Almost all the administered dose was recovered within 48 h (Sauer et al., 1997a).
In a similar experiment in female B6C3F1 mice, the principal urinary metabolites included the glycine conjugates of phenylacetic acid (35%) and benzoic acid (19%), the glutathione conjugate of the ketone (6.7%), and unchanged ketone (8.6%). The principal blood metabolites after intravenous administration of the same dose were the corresponding alcohol and the hydrated ketone 4-hydroxy-4-phenyl-2-butanone, which represented 5.4% and 2.3% of the total dose, respectively. Only about 1.2% of the administered dose was present in the faeces. Approximately 96% was recovered within 48 h (Sauer et al., 1997b).
Carpenter, C.P., Weil, C.S. & Smyth, H.F., Jr (1974) Range-finding toxicity data: List VIII. ., 28, 313–319.
1-phenyl-1,2-propandione + NADH + H+
Ford, G.P., Gopal, T. & Gaunt, I.F. (1983) Short-term toxicity of 4-methyl-1-phenylpentan-2-o1 in rats. .,21, 441–447.
836)), and one aromatic diketone (1-phenyl-1,2-propandione ..
Hopkins, R.P., Borge, P.A. & Callaghan, P. (1972) Dehydrogenation of dl-methylphenylcarbinol in the rat. .,127, 26–27.
Ephedrine from 1-Phenyl-1,2-propanedione: 94 (1)
In Chinchilla rabbits, about 28% of a single dose of 244 mg/kg bw of -methylbenzyl alcohol administered via a stomach tube was excreted in the urine as hippuric acid within 24 h. Rabbits given acetophenone at a single dose of 240 mg/kg bw excreted 19% as hippuric acid (El Masry et al., 1956). Also in rabbits, about 50% of a single oral dose of 450 mg/kg bw -methylbenzyl alcohol was excreted as the glucuronic acid conjugate in urine within 24 h. Other urinary metabolites included hippuric acid (30%) and mandelic acid (1–2%). Under similar conditions, acetophenone underwent essentially the same metabolic fate. An oral dose of 450 mg/kg bw acetophenone was excreted in 24-h urine as the glucuronic acid conjugate of -methylbenzyl alcohol (47%) and as hippuric acid (17%) (Smith et al., 1954a).
The majority (46–61%) of a single dose of benzophenone of 364 mg/kg bw administered to rabbits by stomach tube was excreted as the glucuronide conjugate of the corresponding alcohol, benzhydrol within 48 h (Robinson, 1958). Incubation of a solution of 8 mmol/L benzophenone with rabbit liver homogenate and NADPH resulted in the formation of 20% benzhydrol within 1 h (Leibman, 1971).
1-(4-Chlorophenyl)-1,2-propandione Molecular Weight: 182.60 ..
No data were available on the hydrolysis of the 10 aromatic esters in the group (Nos 800–804, 814, 816, 823, 834, and 835). Hydrolysis of the five -methylbenzyl esters (Nos 800–804) yields the -methylbenzyl alcohol and simple aliphatic carboxylic acids. This conclusion is supported by data on the hydrolysis in vitro of structurally related benzyl esters (benzyl acetate, benzyl 2-methylbutanoate, benzyl cinnamate, and benzyl phenylacetate), which indicate that significant ester hydrolysis is expected before absorption (Leegwater & van Straten, 1974). After absorption, rapid hydrolysis is expected in the blood and liver in vivo. Benzyl acetate was readily hydrolysed in pig liver homogenate (Heymann, 1980). The plasma half-times for the hydrolysis of a series of four alkyl benzoates (including methyl benzoate, ethyl benzoate and propyl benzoate) and two aralkyl benzoates (benzyl benzoate and phenethyl benzoate) in 80% human blood plasma in vitro were 15–210 min (Nielsen & Bundgaard, 1987).
China 1, 3-Propanediol; CAS No: 504-63-2; …
The results of short-term studies were available for 12 of the 38 aromatic substituted secondary alcohols, ketones, and related esters in this group (Brown et al., 1955; Trubek Labs, 1956, 1958; Oser et al., 1965; Hagan et al., 1967; Posternak et al., 1969; Gaunt et al., 1974; National Toxicology Program, 1980; Ford et al., 1983; National Toxicology Program, 1990; Burdock et al., 1991; Freeman et al., 1994). These studies cover a range of structures, including the parent alcohol -methylbenzyl alcohol (No. 799) and its corresponding ketone, acetophenone (No. 806) and acetate ester (No. 801), one naphthyl ketone (methyl -naphthyl ketone (No. 811)), three aromatic secondary alcohols or related esters (1-phenyl-1-propanol (No. 822), the butyric acid ester of 1-phenyl-2-propanol (No. 814), and -isobutylphenethyl alcohol (No. 827)), two -methoxyphenyl-substituted ketones (4-(-methoxyphenyl)-2-butanone (No. 818) and 1-(-methoxyphenyl)-1-penten-3-one (No. 826)), two ketones containing two aromatic rings (benzophenone (No. 831) and benzoin (No. 836)), and one aromatic diketone (1-phenyl-1,2-propandione (No. 833)). The results of these studies are summarized in Table 4 and described below.
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