Gentisic acid
| Gentisic acid[1] | |
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2,5-dihydroxybenzoic acid |
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Other names
DHB |
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| Identifiers | |
| CAS number | 490-79-9  |
| PubChem | 3469 |
| ChemSpider | 3350 |
| UNII | VP36V95O3T |
| KEGG | C00628 |
| ChEBI | CHEBI:17189 |
| ChEMBL | CHEMBL1461 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C7H6O4 |
| Molar mass | 154.12 g/mol |
| Appearance | white to yellow powder |
| Melting point |
200 - 205 C (Sublimes) |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.[2]
[edit] Production
Gentisic acid is produced by carboxylation of hydroquinone.[3]
- C6H4(OH)2 + CO2 → C6H3(CO2H)(OH)2
This conversion is an example of a Kolbe–Schmitt reaction.
[edit] 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, [4] and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI. [5]
[edit] References
- ^ Gentisic acid - Compound Summary, PubChem.
- ^ Levy, G; Tsuchiya, T (1972-09-31). "Salicylate accumulation kinetics in man". New England Journal of Medicine 287 (9): 430–2. doi:10.1056/NEJM197208312870903. PMID 5044917.
- ^ Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_499.
- ^ Strupat K, Karas M, Hillenkamp F (1991). "2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry". Int. J. Mass Spectrom. Ion Processes 72 (111): 89–102. Bibcode 1991IJMSI.111...89S. doi:10.1016/0168-1176(91)85050-V.
- ^ Crumpton, J.; Zhang, W.; Santos, W. L. (2011). "Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry". Analytical Chemistry 83 (9): 3548–3554. doi:10.1021/ac2002565. PMC 3090651. PMID 21449540. http://pubs.acs.org/doi/abs/10.1021/ac2002565.
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