These products are a one-to-one replacement for vanillin and ethyl vanillin.
Vanillin (No. 889) and ethyl vanillin (No. 893)
for hydrochloric acid and 92 or 96% sulfuric acid.Receive, therefore, a two-phase medium consisting of an organic phase containing unreacted substituted phenolic compound, and the aqueous phase containing the expected product, namely salt of 2-hydroxybenzoic acid, at least substituted in position 3 alkoxy group, which is represented by formula I in which 1, Z2and Z3have the meanings given above and M represents a hydrogen atom and/or a cation of a metal of group Ia.Further this is to obtain the aqueous phase.It should be noted that the use as a source of salt hydroxybenzoic acid of the formula II obtained before the actual use, is included in the scope of the invention.At the next stage, the reaction hydroxymethylpropane in position a pair of the OH group by reaction of the salt of the acid obtained above, with formaldehyde, if necessary in the presence of a base.You can use formaldehyde or any connection, forming formaldehyde, such as, for example, trioxane or paraformaldehyde used in the form of linear polyformaldehyde with any degree of polymerization, which is mainly the number of links (CH2O) from 8 to 100.Use the named reagent usually in the form of an aqueous solution having a concentration of less than 50 wt.%, mainly from 20-50 wt.%.The quantity of formaldehyde, expressed in moles of formaldehyde per mole of salt hydroxybenzoic acid may vary over a wide range.Mainly the molar ratio of formaldehyde/salt hydroxybenzoic acid is 0.5 to 3.0.It is possible to conduct the reaction in the presence of a base.
The hydroxy- and alkoxy-substituted benzyl derivatives were inactive in all assays in mammals given the compounds orally or by intraperitoneal injection at doses that were significant fractions of the reported lethal doses. Micronuclei were not induced by -ethoxybenzaldehyde (No. 879) at a dose of 1005 mg/kg bw, ethyl vanillin (No. 893) at 1000 mg/kg bw, vanillin (No. 889) at 500 mg/kg bw, or piperonyl acetate (No. 894) at 620 mg/kg bw (Wild et al, 1983; Furukawa et al, 1989). Piperonal (No. 896) administered by intraperitoneal injection at 1000 mg/kg bw caused a slight increase in the number of early fetal deaths as compared with the incidence in control mice; however, the authors reported that the result was not statistically significant, and no similar finding was reported after administration by oral gavage (Epstein et al, 1972).
Vanillin (No. 889) and ethyl vanillin (No. 893)
About 6% of a dose of 52 mg of 2,4-dihydroxybenzaldehyde (No. 908) given by intraperitoneal injection to female albino rats was excreted in the urine as the corresponding hippurate within 24 h (Teuchy et al., 1971).
Three patients being treated for rheumatic fever were given an oral dose of 5330–6000 mg of 2,4-dihydroxybenzoic acid as 1000 mg per dose every 3 h for 2–16 days. The average daily rate of urinary excretion was 43–76%. The average daily excretion of sulfate conjugate per patient was essentially constant throughout the study, but the average daily excretion of glucuronic acid conjugate increased by four- to sixfold over the 16 days (Clarke et al, 1958). In an investigation of the presence of dihydroxybenzoic acid isomers in the urine of 15 persons, only 3,5-dihydroxybenzoic acid was detected (Williams, 1965).
Vanillin (No. 889) and Ethyl vanillin (No. 893)
Groups of three or more fasted dogs were given butyl -hydroxybenzoate (No. 870) at a dose of 1000 mg/kg bw orally or 50 mg/kg bw intravenously. Blood and urine samples were collected at fixed intervals until the concentrations returned to background values within 48 h. The test material was recovered almost entirely as the -hydroxybenzoic acid conjugate of glucuronic acid, at 48% after the oral dose and 40% after the intravenous dose. Most of the material was excreted between 6 and 30 h after dosing. Although the relatively low rate of recovery with both methods of administration was attributed to incomplete hydrolysis of the ester in the body, incubation of the butyl ester with freshly prepared liver homogenate showed complete hydrolysis within 30–60 min. In studies with related benzoate esters, such as methyl and ethyl -hydroxybenzoate, significantly larger amounts of material were recovered (Jones et al., 1956). This finding suggests that increased amounts of the homologous series of alkyl esters may activate other metabolic and excretion pathways. The authors concluded that butyl -hydroxybenzoate and other alkyl esters are readily absorbed, metabolized, and excreted.
Because of its prevalence and importance as a flavouring agent, vanillin (No. 889) has been the subject of numerous studies on metabolism. Male albino rats were given 100 mg/kg bw of vanillin in a solution of propylene glycol and water by stomach tube; urine and faeces were collected separately for 24-h periods, and bile samples were collected by cannulation of the common bile duct. Only trace amounts of benzoic acid derivatives remained in the urine after the first 24 h, and none remained after 48 h. Free and conjugated forms of vanillic acid and vanillyl alcohol accounted for 94% of the dose in the urine. Vanillin and its primary reduction and oxidation metabolites were also excreted in appreciable amounts in the bile. Bile collected for 5 h from two rats given vanillin at a dose of 100 or 300 mg/kg bw orally contained glucuronide conjugates of vanillin (6%), vanillyl alcohol (8%), and vanillic acid (9%) (Strand & Scheline, 1975).
phosphonothioic dichloride, ethyl- (CAS 993-43-1)
Vanillin Synthesis from 4-Hydroxybenzaldehyde - …
1.10 References Beilstein : 6(3)4307 « 3-Ethoxy-4-hydroxybenzaldehyde Ethyl Propyl Ether » Page Top ...
Vanillin Synthesis from 4-Hydroxybenzaldehyde
Veratraldehyde (No. 877), vanillin (No. 889), ethyl vanillin (No. 893), and piperonal (No. 896)
Synthesis of Vanillin from 4-hydroxybenzaldehyde by …
1,1,3,3,3-Pentafluoro-2-trifluoromethyl-1-propene (CAS 382-21-8) and ethylene dibromide (EDB) (CAS 106-93-4))
4-hydroxybenzaldehyde, 123-08-0 - The Good Scents …
In a similar study, groups of four to eight rabbits were given 4-hydroxybenzoic acid (No. 957) at a dose of 100, 250, 500, 1000, or 1500 mg/kg bw by gavage every 3–7 days. Urine was collected continuously and analysed for metabolites. The total urinary recovery of the test material ranged from 84% to 104% . Glucuronic acid and sulfate conjugates were also detected in the urine, at 10–35% and 4–7%, respectively. The concentrations of all the metabolites returned to background values within 24 h after dosing (Bray et al., 1947). In a corresponding study, approximately 94% of 2-hydroxybenzoic acid (No. 958) at a single oral dose of 250 or 500 mg/kg bw given to two groups of four rabbits was excreted unchanged or as the glucuronic acid and sulfate conjugates (Bray et al., 1948).
3-Ethoxy-4-hydroxybenzaldehyde | C9H10O3 - PubChem
After administration of a single dose of 400 mg/kg bw of salicylaldehyde (No. 897) to a fasted rabbit, 75% of the dose was excreted in urine collected over 24 h. Urine analysis revealed mainly ether-soluble acids, 27% and 3% being accounted for by glucuronic acid and sulfate conjugates of vanillic acid, respectively (Bray et al., 1952).
ethyl vanillin, 121-32-4 - The Good Scents Company
An oral dose of methyl salicylate (No. 899) equivalent to 500 mg/kg bw of salicylic acid was dissolved in 2% methyl cellulose and given to male rats. The plasma concentrations measured within 20 min of dosing showed complete hydrolysis of methyl salicylate. In a similar experiment with three fasted male dogs given 320 mg/kg bw of methyl salicylate in capsules, blood drawn 1 h after dosing showed 95% hydrolysis of methyl salicylate to salicylic acid. In six persons, 79% of a dose of 0.42 ml (approximately 500 mg) of methyl salicylate administered in ginger ale was hydrolysed in the blood within 90 min (Davison et al., 1961).
ethyl vanillin 121-32-4 Route Of Synthesis _ Synthetic …
Several experiments were conducted to study the metabolism of esters of -hydroxybenzoic acid after oral (1000 mg/kg bw) or intravenous (50 mg/kg bw) administration to dogs. The esters were absorbed in the gastrointestinal tract and rapidly hydrolysed by esterases in the liver and kidney. In the case of butyl -hydroxybenzoate (No. 870), 48% was recovered after oral and 40% after intravenous administration. Liver preparations from dogs injected with 100 mg/kg bw of the methyl, ethyl, or propyl ester showed 100% hydrolysis within 3 min. In the case of the butyl ester, 100% hydrolysis occurred within 30–60 min (Jones et al., 1956).
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