| 2,5-Dihydroxybenzoic acid Basic information |
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| 2,5-Dihydroxybenzoic acid Chemical Properties |
| Melting point |
204-208 °C(lit.) |
| Boiling point |
237.46°C (rough estimate) |
| density |
1.3725 (rough estimate) |
| refractive index |
1.6400 (estimate) |
| storage temp. |
Store below +30°C. |
| solubility |
It is soluble in alcohol and r. |
| pka |
2.97(at 25℃) |
| form |
Crystalline Powder |
| color |
White to light beige |
| Water Solubility |
soluble |
| Merck |
14,4398 |
| BRN |
2209119 |
| InChIKey |
WXTMDXOMEHJXQO-UHFFFAOYSA-N |
| CAS DataBase Reference |
490-79-9(CAS DataBase Reference) |
| NIST Chemistry Reference |
2,5-Dihydroxybenzoic acid(490-79-9) |
| EPA Substance Registry System |
Benzoic acid, 2,5-dihydroxy- (490-79-9) |
| Hazard Codes |
Xn,Xi |
| Risk Statements |
22-36/37/38 |
| Safety Statements |
26-36-37/39 |
| WGK Germany |
3 |
| RTECS |
LY3850000 |
| Hazard Note |
Harmful |
| TSCA |
Yes |
| HS Code |
29182990 |
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| 2,5-Dihydroxybenzoic acid Usage And Synthesis |
| Description |
Gentisic acid is a dihydroxy benzoic acid. It is a derivative of benzoic acid and a minor (1 %) product of the metabolic break down of aspirin, excreted by the kidneys.
It is also found in the African tree Alchornea cordifolia and in wine. |
| Chemical Properties |
white to light beige crystalline powder |
| Uses |
Medicine, as sodium gentisate (analgesic). |
| Definition |
ChEBI: A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. |
| Production Methods |
Gentisic acid is produced by carboxylation of hydroquinone.
C6H4(OH)2 + CO2 → C6H3(CO2H)(OH)2
This conversion is an example of a Kolbe–Schmitt reaction. |
| Application |
As a hydroquinone , gentisic acid is readily oxidized 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 , and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI . |
| Synthesis Reference(s) |
Journal of the American Chemical Society, 72, p. 3292, 1950 DOI: 10.1021/ja01163a521 |
| Safety Profile |
Poison bp intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. |
| Purification Methods |
Crystallise gentisic acid from hot water or *benzene/. Dry it in a vacuum desiccator over silica gel. [Beilstein 10 H 384, 10 IV 1441.] |
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| 2,5-Dihydroxybenzoic acid Preparation Products And Raw materials |
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