2,3-Dihydroxybenzoic acid
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| 2,3-Dihydroxybenzoic acid | |
|---|---|
 |
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| IUPAC name | 2,3-Dihydroxybenzoic acid |
| Other names | 2,3-DHB |
| Identifiers | |
| CAS number | [303-38-8] |
| Properties | |
| Molecular formula | C12H10O |
| Molar mass | 154.12 |
| Appearance | Colorless solid |
| Melting point |
204-206 °C |
| Solubility in water | low |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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2,3-Dihydroxybenzoic acid is the organic compound with the formula C6H3(OH)2CO2H. The colourless solid occurs naturally, being formed via the Chorismic acid pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents lined to the depsitripeptide of serine.[1]
[edit] References
- ^ I. G. O'Brien, G. B. Cox, F. Gibson "Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli" Biochim Biophys Acta 1970 Volume 201, 453-60.
