Gentisic acid
Names | |
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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 ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.007.017 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C7H6O4 | |
Molar mass | 154.12 g/mol |
Appearance | white to yellow powder |
Melting point | 204 °C (399 °F; 477 K)[3] |
Acidity (pKa) | 2.97[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
It is also found in the African tree Alchornea cordifolia and in wine.[5]
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]
Reactions
In the presence of the enzyme
maleylpyruvate
:
- 2,5-dihydroxybenzoate + O2 maleylpyruvate
Applications
As a
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]
References
- ^ Gentisic acid - Compound Summary, PubChem.
- ^ Haynes, p. 5.91
- ^ Haynes, p. 3.190
- PMID 5044917.
- PMC 6253884.
- .
- ISBN 978-0471832539.
- .
- .
- PMID 21449540.
Cited sources
- Haynes, William M., ed. (2016). ISBN 9781498754293.