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Gallic acid information


Gallic acid
Skeletal formula
Space-filling model of gallic acid
Names
Preferred IUPAC name
3,4,5-Trihydroxybenzoic acid
Other names
Gallic acid
Identifiers
CAS Number
  • 149-91-7 checkY
  • 5995-86-8 (monohydrate) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:30778 checkY
ChEMBL
  • ChEMBL288114 checkY
ChemSpider
  • 361 checkY
ECHA InfoCard 100.005.228 Edit this at Wikidata
EC Number
  • 205-749-9
IUPHAR/BPS
  • 5549
KEGG
  • C01424 checkY
PubChem CID
  • 370
RTECS number
  • LW7525000
UNII
  • 632XD903SP checkY
  • 48339473OT (monohydrate) checkY
CompTox Dashboard (EPA)
  • DTXSID0020650 Edit this at Wikidata
InChI
  • InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12) checkY
    Key: LNTHITQWFMADLM-UHFFFAOYSA-N checkY
  • 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
Chemical formula
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)
Solubility in water
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability (yellow): no hazard codeSpecial hazards (white): no code
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 checkY☒N ?)
Infobox references

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.[1] It is a white solid, although samples are typically brown owing to partial oxidation. Salts and esters of gallic acid are termed "gallates".

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

  1. ^ Haslam, E.; Cai, Y. (1994). "Plant polyphenols (vegetable tannins): Gallic acid metabolism". Natural Product Reports. 11 (1): 41–66. doi:10.1039/NP9941100041. PMID 15206456.

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Gallic acid

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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...

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Shikimic acid

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spontaneously rearranges to gallic acid. Shikimic acid is a precursor for: indole, indole derivatives and aromatic amino acid tryptophan and tryptophan...

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Gallic

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the name gallic acid, for a phenolic compound found in these formations 'Gallic' is also a proper noun naming the following ships: SS Gallic (1894), a...

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Tannin

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times. Tannins have molecular weights ranging from 500 to over 3,000 (gallic acid esters) and up to 20,000 daltons (proanthocyanidins). There are three...

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Ellagic acid

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the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide. Ellagic acid is found in oak species such as the North...

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Tannic acid

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reactions as gallotannic acid. It differs however from the latter in not being convertible into gallic acid, and not yielding pyrogallic acid by dry distillation...

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Polyphenol

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raspberry ellagitannin, on the other hand, with its 14 gallic acid moieties (most in ellagic acid-type components), and more than 40 phenolic hydroxyl groups...

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Iron gall ink

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name. Fermentation or hydrolysis of the extract releases glucose and gallic acid, which yields a darker purple-black ink, due to the formation of iron...

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Pyrogallol

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manner first reported by Scheele in 1786: heating gallic acid to induce decarboxylation. Gallic acid is also obtained from tannin. Many alternative routes...

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Hydrolysable tannin

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of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids. At the center of a hydrolysable tannin molecule, there...

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Gallic acid reagent

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sulfuric acid. 0.05 g of gallic acid is used for every 10 mls of sulfuric acid. The same ratio of gallic acid n-propyl ester in sulfuric acid can also...

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Eudesmic acid

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acid is an O-methylated trihydroxybenzoic acid. It can be found in Eucalyptus spp. Eudesmic acid is most directly synthesized by reaction of gallic acid...

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Syringic acid

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acid pathway in plants. Syringic acid can be prepared by selectively hydrolyzing (demethylating) eudesmic acid with 20% sulfuric acid. Syringic acid can...

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Pittosporum tobira

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acid (20.07 mg/g), p-coumaric acid (12.85 mg/g), cinnamic acid (5.14 mg/g), and gallic acid (1.03 mg/g). Nineteen components were found to makeup 89.5%...

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Mango

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alpha-carotene, and polyphenols, such as quercetin, kaempferol, gallic acid, caffeic acid, catechins and tannins. Mango contains a unique xanthonoid called...

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Hexahydroxydiphenic acid

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Hexahydroxydiphenic acid is an organic compound with the formula [(HO)3C6HCO2H]2. It is the oxidatively coupled derivative of gallic acid It is a white solid...

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Gallotannin

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belonging to the hydrolysable tannins. Gallotannins are polymers formed when gallic acid, a polyphenol monomer, esterifies and binds with the hydroxyl group of...

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Epigallocatechin gallate

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as epigallocatechin-3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin. EGCG – the most abundant catechin in tea...

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Bergenia ciliata

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Northern Nepal, Bhutan (Haa and Mongar districts). Bergenin, catechin, gallic acid, gallicin, catechin-7-O-glucoside and β-sitosterol can be found in B...

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Naturally occurring phenols

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polymerized, creating a new class of polyphenol. For example, ellagic acid is a dimer of gallic acid and forms the class of ellagitannins, or a catechin and a gallocatechin...

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Ethyl gallate

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gallate is a food additive with E number E313. It is the ethyl ester of gallic acid. Ethyl gallate is added to food as an antioxidant. Though found naturally...

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Propyl gallate

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propyl 3,4,5-trihydroxybenzoate is an ester formed by the condensation of gallic acid and propanol. Since 1948, this antioxidant has been added to foods containing...

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Methyl gallate

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Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid. It is found in Terminalia myriocarpa, Bergenia ciliata (hairy Bergenia)...

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Eugenol

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(2004). "TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove". Chromatographia. 60 (3–4): 241–244. doi:10.1365/s10337-004-0373-y...

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Terminalia chebula

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with gallic acids called chebulin, as well as other phenolic compounds including ellagic acid, 2,4-chebulyl-β-D-glucopyranose, chebulinic acid, gallic acid...

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Clove

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the 1911 Encyclopædia Britannica article "Cloves". Cinnamomum cassia Gallic acid Insect repellent Medicinal plant "Syzygium aromaticum (L.) Merr. & L...

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Bergenia

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from the appearance of the plant. Bergenin, C-glycoside of 4-O-methyl gallic acid, and its O-demethylated derivative norbergenin, are chemical compounds...

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Raspberry

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pigments, ellagic acid, ellagitannins, quercetin, gallic acid, cyanidins, pelargonidins, catechins, kaempferol and salicylic acid. Yellow raspberries...

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