4-allyl-2-methoxyphenol properties - SpringerMaterials

Alkoxyphenols are excreted mainly as glucuronic acid or sulfate conjugates. The presence of both methoxy and hydroxy functions activates the ring towards further substitution, which may lead to the formation of polyphenols. In humans, 73% of a 50-mg dose of guaiacol (2-methoxyphenol; No. 713) was excreted as the sulfate and glucuronic acid conjugates within 14 h (Sedivec & Flek, 1970); however, the period of urine collection was not specified. In cats, a single oral dose of 2,6-dimethoxyphenol (No. 721) at 20 or 40 mg/kg bw was excreted mainly as conjugated 2,6-dimethoxy-4-hydroxyphenol after demethylation (90% as disulfate) and as unconjugated (3%) 2,6-dimethoxy-4-hydroxyphenol within 24 h of dosing. Free (5%) and conjugated (2% with glucuronic acid) forms of the parent phenol were also detected (Miller et al., 1976).Like the -alkylphenols, 2-methoxy-4-alkylphenols can form electrophilic quinone methide intermediates at high cellular concentrations. 2-Methoxy-4-methylphenol (No. 715), 2-methoxy-4-propylphenol (No. 717), 2-methoxy-4-vinylphenol (No. 725), and 4-allyl-2,6-dimethoxyphenol (No. 726) were oxidized to quinone methides in rat liver slices in vitro. The half-lives of the quinone methides formed from these substances were 1, 6, 410, and 4300 s, respectively. Hepatocellular toxicity, measured as intracellular potassium leakage, was detected in rat liver slices incubated with each phenol for 6 h. These findings suggest that only quinone methides with half-lives of 10 s to 10 min are reactive enough to be cytotoxic at high concentrations (Thompson et al., 1995a).Phenol derivatives with an alkyl side-chain containing a ketone function (Nos 727-732)The presence of a ketone functiona confers the possibility of rapid metabolism like that of related phenols. Zingerone (3-methoxy-4-hydroxybenzylacetone; No. 730) given to rats as a single oral or intraperitoneal dose of 100 mg/kg bw was excreted in the urine mainly as glucuronic acid and sulfate conjugates. Reduction of the ketone to zingerol (12%) was also observed, with lesser ring hydroxylation to 4(3,4-dihydroxyphenyl)-2-butanone (6%) and side-chain oxidation to 4-hydroxy-3-methoxyphenylacetic acid (8%) (Monge et al., 1976).The closely related 4-(-hydroxyphenyl)-2-butanone (No. 728), the phenol derivative produced in the highest volume, would be expected to be metabolized by essentially the same pathways.Studies-lasting 90 days and longer-term studies of toxicity and carcinogenicity were available for 12 of the 48 substances in this group and addressed-all four structural categories of phenol derivatives. Five concerned phenol or resorcinol (National Toxicology Program, 1980; Hirose et al., 1986, 1989; Maruyama et al., 1991; National Toxicology Program, 1992b), 12 were conducted with alkyl- or aryl-substituted phenols, and their corresponding esters (Hodge et al., 1952; Hagan et al., 1967; Posternak & Linder, 1969; Maasik, 1970; Hagiwara et al., 1984; Hiraga & Fujii, 1984; Hirose et al., 1986; Environmental Protection Agency, 1988a,b; National Toxicology Program, 1992a; Quast et al., 1997; Wahle et al., 1997), one was carried out with alkoxy phenols (Posternak & Linder, 1969), and two addressed phenol derivatives with an alkyl side-chain containing a ketone function (Gaunt et al., 1970; Kociba et al., 1976).(No. 735)

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Properties frequently appearing with 4-allyl-2-methoxyphenol dielectric constant ..
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4-allyl-2-bromo-6-methoxyphenol | C10H11BrO2 - …

The presence of a ketone functiona confers the possibility of rapid metabolism like that of related phenols. Zingerone (3-methoxy-4-hydroxybenzylacetone; No. 730) given to rats as a single oral or intraperitoneal dose of 100 mg/kg bw was excreted in the urine mainly as glucuronic acid and sulfate conjugates. Reduction of the ketone to zingerol (12%) was also observed, with lesser ring hydroxylation to 4(3,4-dihydroxyphenyl)-2-butanone (6%) and side-chain oxidation to 4-hydroxy-3-methoxyphenylacetic acid (8%) (Monge et al., 1976).

2 allyl 4 methoxyphenol | scholarly search

Experiments with anisole in vivo confirm that ring-hydroxylation predominates over -demethylation. Analysis of urine collected from rabbits 24 h after treatment by gavage with anisole at a dose of 0.5 g/kg bw revealed that 2% of the excreted anisole was unconjugated, 48% was conjugated with glucuronic acid, and 29% was conjugated with sulfate. The metabolites of anisole are -methoxyphenol (major) and -methoxyphenol (minor). No evidence of ether cleavage was detected in either anisole or diphenyl ether (Bray et al., 1953). Incubation of anisole (2 mmol) with rabbit liver microsomes for 1 h resulted in ether cleavage to phenol and formaldehyde at a relative enzymatic dealkylation rate of 6% from -ethoxyacetanilide to acetamidophenol. The results of this study demonstrate that anisole undergoes limited ether cleavage in the rabbit (Axelrod, 1956).

synthesis and optimization of cyclopropanation process of 4-allyl-2-methoxyphenol
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4-methoxyphenol for synthesis 1x250gms : 1 :

Groups of 20-32 male and female Charles River CD rats were fed a basal diet supplemented with 2,6-dimethoxyphenol (No. 721) for 90 days, providing average intakes of 6.0 mg/kg bw per day for males and 6.8 mg/kg bw per day for females. A control group was fed the basal diet alone. Weekly measurements of body weight, food consumption, and calculated efficiency of food use showed no significant differences from controls. Haematological and clinical chemical examinations at weeks 7 and 13 showed no effects. At necropsy, there were no significant changes in liver or kidney weights. Gross and histological examination of a wide range of organs (unspecified in the report) revealed no lesions related to treatment with either substance. The NOEL was 6.0 mg/kg bw per day (Posternak & Linder, 1969).

4-(1,3-dithiolan-2-yl)-2-methoxyphenol

Like the -alkylphenols, 2-methoxy-4-alkylphenols can form electrophilic quinone methide intermediates at high cellular concentrations. 2-Methoxy-4-methylphenol (No. 715), 2-methoxy-4-propylphenol (No. 717), 2-methoxy-4-vinylphenol (No. 725), and 4-allyl-2,6-dimethoxyphenol (No. 726) were oxidized to quinone methides in rat liver slices in vitro. The half-lives of the quinone methides formed from these substances were 1, 6, 410, and 4300 s, respectively. Hepatocellular toxicity, measured as intracellular potassium leakage, was detected in rat liver slices incubated with each phenol for 6 h. These findings suggest that only quinone methides with half-lives of 10 s to 10 min are reactive enough to be cytotoxic at high concentrations (Thompson et al., 1995a).

Aceteugenol; 4-Allyl-2-methoxyphenyl acetate More..

Alkoxyphenols are excreted mainly as glucuronic acid or sulfate conjugates. The presence of both methoxy and hydroxy functions activates the ring towards further substitution, which may lead to the formation of polyphenols. In humans, 73% of a 50-mg dose of guaiacol (2-methoxyphenol; No. 713) was excreted as the sulfate and glucuronic acid conjugates within 14 h (Sedivec & Flek, 1970); however, the period of urine collection was not specified. In cats, a single oral dose of 2,6-dimethoxyphenol (No. 721) at 20 or 40 mg/kg bw was excreted mainly as conjugated 2,6-dimethoxy-4-hydroxyphenol after demethylation (90% as disulfate) and as unconjugated (3%) 2,6-dimethoxy-4-hydroxyphenol within 24 h of dosing. Free (5%) and conjugated (2% with glucuronic acid) forms of the parent phenol were also detected (Miller et al., 1976).