Gentisic acid

Chemical compound From Wikipedia, the free encyclopedia

Gentisic acid

Gentisic acid is a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, excreted by the kidneys.[4]

Quick Facts Names, Identifiers ...
Gentisic acid[1]
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Names
Preferred IUPAC name
2,5-Dihydroxybenzoic acid
Other names
DHB
5-Hydroxysalicylic acid
Gentianic acid
Carboxyhydroquinone
2,5-Dioxybenzoic Acid
Hydroquinonecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.017 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) checkY
    Key: WXTMDXOMEHJXQO-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
    Key: WXTMDXOMEHJXQO-UHFFFAOYAO
  • O=C(O)c1cc(O)ccc1O
Properties
C7H6O4
Molar mass 154.12 g/mol
Appearance white to yellow powder
Melting point 204 °C (399 °F; 477 K)[2]
Acidity (pKa) 2.97[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is also found in the African tree Alchornea cordifolia and in wine.[5]

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Production

Gentisic acid is produced by carboxylation of hydroquinone.[6]

C6H4(OH)2 + CO2 → C6H3(CO2H)(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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Reactions

In the presence of the enzyme gentisate 1,2-dioxygenase, gentisic acid reacts with oxygen to give maleylpyruvate:

2,5-dihydroxybenzoate + O2 maleylpyruvate

Applications

As a hydroquinone, gentisic acid is readily oxidised and is used as an antioxidant excipient in some pharmaceutical preparations.

In the laboratory, it is used as a sample matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry,[9] and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI.[10]

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References

Cited sources

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