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It is prepared by disulfonation of benzoic acid followed by hydrolysis of the disulfonate. [ 3 ] It is a metabolite of alkylresorcinols , first identified in human urine [ 4 ] and can be quantified in urine [ 5 ] and plasma, [ 6 ] and may be an alternative, equivalent biomarker of whole grain wheat intake.
Dihydroxybenzoic acids (DHBA) are a type of phenolic acids. There are six main compounds, having all the same molecular formula C 7 H 6 O 4. Those are: 2,3-Dihydroxybenzoic acid (2-Pyrocatechuic acid or hypogallic acid) 2,4-Dihydroxybenzoic acid (β-Resorcylic acid) 2,5-Dihydroxybenzoic acid (Gentisic acid) 2,6-Dihydroxybenzoic acid (γ ...
2,3-diDHB dehydrogenase catalyzes the NAD +-dependent oxidation of 2,3-dihydro-2,3-dihydroxybenzoate to produce an aromatic compound 2,3-dihydroxybenzoic acid (2,3-DHB or simply DHB). [4] In times of iron deficiency, iron uptake is controlled by three genes: ent , fep , and fes for synthesis, export, and uptake of ferric Enterobactin and its ...
Addition to the aromatic ring results in an intermediate at the oxidation state of a benzylamine. An intramolecular redox reaction then ensues, raising the benzylic carbon to the oxidation state of an aldehyde. The oxygen atom is provided by water on acid hydrolysis in the final step. Duff reaction mechanism
2,4-Dihydroxybenzoic acid (β-resorcylic acid) is a dihydroxybenzoic acid. As a resorcylic acid, it is one of the three isomeric crystalline acids that are both carboxyl derivatives of resorcinol and dihydroxy derivatives of benzoic acid. [4] Synthesis from resorcinol is via the Kolbe-Schmitt reaction. [5]
The reaction is acid catalyzed and the reaction type is nucleophilic addition of the amine to the carbonyl compound followed by transfer of a proton from nitrogen to oxygen to a stable hemiaminal or carbinolamine. With primary amines, water is lost in an elimination reaction to an imine. With aryl amines, especially stable Schiff bases are formed.
Gentisic acid is produced by carboxylation of hydroquinone. [6] C 6 H 4 (OH) 2 + CO 2 → C 6 H 3 (CO 2 H)(OH) 2. This conversion is an example of a Kolbe–Schmitt reaction. Alternatively the compound can be synthesized from salicylic acid via Elbs persulfate oxidation. [7] [8]
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