Chemical Properties
Pale Brownish to Red Brownish Crystalline Powder. 2,3-Dihydroxybenzoic Acid [303-38-8],
C7H6O4, Mr 154.1, mp 206℃, undergoes decomposition to catechol and carbon dioxide. The
acid crystallizes from water as a dihydrate.
Among other uses, it serves as an iron-complexing agent in drugs.
Uses
2,3-Dihydroxybenzoic Acid is a selected phenol as MMP (Matrix Metalloproteinase) inhibitor.
Uses
2,3-Dihydroxybenzoic acid was used to study the complexes of manganese with aliphatic and aromatic polyhydroxy ligands in basic media by electrochemical, spectrophotometric and magnetic methods. It was used in isolation of new siderophore named vulnibactin from low iron cultures of
Vibrio vulnificus, a human pathogen. It was used as cocrystal former to study the influence of position isomerism on the co-crystals formation and physicochemical properties of piracetam.
Definition
ChEBI: A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.
Biochem/physiol Actions
2,3-Dihydroxybenzoic acid was found to be orally effective iron-chelating drug in hypertransfused rat model. It is monocatechol siderophore produced by Brucella abortus.
Synthesis
There are two main routes for the preparation of 2,3-dihydroxybenzoic acid (2,3-DHBA): chemical synthesis and biosynthesis. The classic chemical synthesis method is the carboxylation of catechol, similar to the Kolbe-Schmidt reaction. This method typically involves reacting catechol with an alkali metal salt (such as sodium or potassium salt) under high temperature (approximately 200°C) and high pressure (several megapascals) carbon dioxide atmosphere, resulting in the substitution of the ortho- and ortho-positions of the benzene ring with a carboxyl group (-COOH). Subsequent acidification yields the target product. Furthermore, with the development of green chemistry, biosynthesis has also become an important preparation method. For example, specific microorganisms or enzymes (such as the reverse reaction of 2,3-dihydroxybenzoic acid decarboxylase) can be used to achieve the carboxylation of catechol, or 2,3-dihydroxybenzoic acid can be prepared through the 3-hydroxylation of salicylic acid.
