Gallic acid
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| Names | |||
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Preferred IUPAC name
3,4,5-Trihydroxybenzoic acid
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| Other names
Gallic acid
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| Identifiers | |||
149-91-7  5995-86-8 (monohydrate) 
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| 3D model (Jmol) | Interactive image | ||
| ChEBI |
CHEBI:30778
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| ChEMBL |
ChEMBL288114
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| ChemSpider |
361
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| ECHA InfoCard | 100.005.228 | ||
| EC Number | 205-749-9 | ||
| 5549 | |||
| KEGG |
C01424
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| PubChem | 370 | ||
| RTECS number | LW7525000 | ||
| UNII |
632XD903SP
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| Properties | |||
| C7H6O5 | |||
| Molar mass | 170.12 g/mol | ||
| Appearance | White, yellowish-white, or pale fawn-colored crystals. |
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| Density | 1.694 g/cm3 (anhydrous) | ||
| Melting point | 260 °C (500 °F; 533 K) | ||
| 1.19 g/100 mL, 20°C (anhydrous) 1.5 g/100 mL, 20 °C (monohydrate) |
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| Solubility | soluble in alcohol, ether, glycerol, acetone negligible in benzene, chloroform, petroleum ether |
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| log P | 0.70 | ||
| Acidity (pKa) | COOH: 4.5, OH: 10. | ||
| -90.0·10−6 cm3/mol | |||
| Hazards | |||
| Main hazards | Irritant | ||
| Safety data sheet | External MSDS | ||
| NFPA 704 | |||
| Lethal dose or concentration (LD, LC): | |||
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LD50 (median dose)
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5000 mg/kg (rabbit, oral) | ||
| Related compounds | |||
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Related
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phenols, carboxylic acids |
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Related compounds
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Benzoic acid, Phenol, Pyrogallol | ||
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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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 (what is ?) |
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| Infobox references | |||
Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid, a type of phenolic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula of gallic acid is C6H2(OH)3COOH. Gallic acid is found both free and as part of hydrolyzable tannins. The gallic acid groups are usually bonded to form dimers such as ellagic acid. Hydrolyzable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins respectively.
Gallic acid forms intermolecular esters (depsides) such as digallic and trigallic acids, and cyclic ether-esters (depsidones).
Gallic acid is commonly used in the pharmaceutical industry. It is used as a standard for determining the phenol content of various analytes by the Folin-Ciocalteau assay; results are reported in gallic acid equivalents. Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline.
The name is derived from oak galls, which were historically used to prepare tannic acid. Despite the name, gallic acid does not contain gallium. Salts and esters of gallic acid are termed "gallates".
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