Gallic acid

Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6H2(OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. It is a white solid, although samples are typically brown owing to partial oxidation. Salts and esters of gallic acid are termed "gallates".

Gallic acid
Names
Preferred IUPAC name
3,4,5-Trihydroxybenzoic acid
Other names
Gallic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.228
EC Number
  • 205-749-9
KEGG
PubChem CID
RTECS number
  • LW7525000
UNII
  • InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12) Y
    Key: LNTHITQWFMADLM-UHFFFAOYSA-N Y
  • InChI=1/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
    Key: LNTHITQWFMADLM-UHFFFAOYAN
SMILES
  • O=C(O)c1cc(O)c(O)c(O)c1
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.
Magnetic susceptibility (χ)
-90.0·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
NFPA 704 (fire diamond)
1
0
Lethal dose or concentration (LD, LC):
LD50 (median dose)
5000 mg/kg (rabbit, oral)
Safety data sheet (SDS) External MSDS
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 verify (what is YN ?)
Infobox references

Its name is derived from oak galls, which were historically used to prepare tannic acid. Despite the name, gallic acid does not contain gallium.

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