Gentisic acid
| Skeletal formula of gentisic acid | |
| Space-filling model of the gentisic acid molecule | |
| Names | |
|---|---|
| IUPAC name
2,5-dihydroxybenzoic acid
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| Other names
DHB
2,5-dihydroxybenzoic acid 5-Hydroxysalicylic acid Gentianic acid Carboxyhydroquinone 2,5-Dioxybenzoic Acid Hydroquinonecarboxylic acid |
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| Identifiers | |
490-79-9  |
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| ChEBI | CHEBI:17189 |
| ChEMBL | ChEMBL1461 |
| ChemSpider | 3350 |
| Jmol 3D model | Interactive image |
| KEGG | C00628 |
| PubChem | 3469 |
| UNII | VP36V95O3T |
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| Properties | |
| C7H6O4 | |
| Molar mass | 154.12 g/mol |
| Appearance | white to yellow powder |
| Melting point | 200 to 205 °C (392 to 401 °F; 473 to 478 K) (Sublimes) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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]
It is also found in the African tree Alchornea cordifolia and in wine.[3]
Production
Gentisic acid is produced by carboxylation of hydroquinone.[4]
- 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 (50% yield).[5][6]
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,[7] and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI.[8]
References
- ↑ Gentisic acid - Compound Summary, PubChem.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times. Rong-Rong Tian, Qiu-Hong Pan, Ji-Cheng Zhan, Jing-Ming Li, Si-Bao Wan, Qing-Hua Zhang and Wei-Dong Huang, Molecules, 2009, 14, pages 827-838, doi:10.3390/molecules14020827
- ↑ 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.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
