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|Reference=<ref>[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3469&loc=ec_rcs Gentisic acid - Compound Summary], [[PubChem]].</ref> |
|Reference=<ref>[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3469&loc=ec_rcs Gentisic acid - Compound Summary], [[PubChem]].</ref> |
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Revision as of 09:27, 29 November 2010
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| Names | |
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| IUPAC name
2,5-dihydroxybenzoic acid
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| Other names
5-Hydroxysalicylic acid; Gentianic acid; Carboxyhydroquinone; 2,5-Dioxybenzoic Acid; Hydroquinonecarboxylic Acid
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.017 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H6O4 | |
| Molar mass | 154.12 |
| Appearance | white to yellow powder |
| Melting point | 200 - 205 C (Sublimes) |
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, or 2,5-dihydroxybenzoic acid (DHB), is a derivatives of benzoic acid. It is one of several dihydroxybenzoic acids. It is a minor (1%) product of the metabolic break down of aspirin, excreted by the kidneys[2].
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.
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]
References
- ^ Gentisic acid - Compound Summary, PubChem.
- ^ Levy, G (1972-09-31). "Salicylate accumulation kinetics in man". New England Journal of Medicine. 287 (9): 430–2. doi:10.1056/NEJM197208312870903. PMID 5044917.
{{cite journal}}: Check date values in:|date=(help); Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ 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. doi:10.1016/0168-1176(91)85050-V.
{{cite journal}}: CS1 maint: multiple names: authors list (link)