2,3-Dihydroxybenzoic acid
Chemical compound
From Wikipedia, the free encyclopedia
2,3-Dihydroxybenzoic acid is a dihydroxybenzoic acid, a type of organic compound. It occurs naturally in various plants, bacteria, and fungi.
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| Names | |
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| Preferred IUPAC name
2,3-Dihydroxybenzoic acid | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| Abbreviations |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.005.582 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties[1] | |
| C7H6O4 | |
| Molar mass | 154.121 g·mol−1 |
| Appearance | Colorless solid |
| Density | 1.542 g/cm3 (20 °C) |
| Melting point | 205 °C (401 °F; 478 K) |
| soluble | |
| Solubility in ethanol | soluble |
| Solubility in diethyl ether | soluble |
| Solubility in acetone | soluble |
| Related compounds | |
Related compounds |
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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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Uses
It is a potentially useful iron-chelating drug and has antimicrobial properties.[2][3][medical citation needed]
Occurrence
It is found in Phyllanthus acidus[citation needed] and in the aquatic fern Salvinia molesta.[4] It is also abundant in the fruits of Flacourtia inermis.[2]
The colorless solid occurs naturally, being formed via the shikimate pathway.[citation needed] 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 through amide bonds. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsipeptide of serine.[5]
2,3-Dihydroxybenzoic acid is also a product of human aspirin metabolism.[6]