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Gallic acid

Gallic acid
Gallic acid.svg
Ácido gálico.png
Names
Preferred IUPAC name
3,4,5-Trihydroxybenzoic acid
Other names
Gallic acid
Identifiers
149-91-7 YesY
5995-86-8 (monohydrate) N
3D model (Jmol) Interactive image
ChEBI CHEBI:30778 YesY
ChEMBL ChEMBL288114 YesY
ChemSpider 361 YesY
ECHA InfoCard 100.005.228
EC Number 205-749-9
5549
KEGG C01424 YesY
PubChem 370
RTECS number LW7525000
UNII 632XD903SP YesY
Properties
C7H6O5
Molar mass 170.12 g/mol
Appearance White, yellowish-white, or
pale fawn-colored crystals.
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)
Solubility soluble in alcohol, ether, glycerol, acetone
negligible in benzene, chloroform, petroleum ether
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
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Lethal dose or concentration (LD, LC):
LD50 (median dose)
5000 mg/kg (rabbit, oral)
Related compounds
Related
phenols,
carboxylic acids
Related compounds
Benzoic acid, Phenol, Pyrogallol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
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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