Gallic acid Information & Gallic acid Links at HealthHaven.com

Gallic acid
IUPAC name	3,4,5-trihydroxybenzoic acid
Other names	Gallic acid; Gallate; 3,4,5-trihydroxybenzoate
Identifiers
CAS number	149-91-7 ,[5995-86-8] (Monohydrate)
PubChem	370
SMILES	Oc1cc(cc(O)c1O)C(O)=O
Properties
Molecular formula	C7H6O5
Molar mass	170.12 g/mol
Exact mass	170.021523
Appearance	White, yellowish-white, or; pale fawn-colored crystals.
Density	1.7 g/cm3 (anhydrous)
Melting point	250 °C, 523 K, 482 °F
Solubility in water	1.1 g/100 ml water @ 20°C (anhydrous); 1.5 g/100 ml water @ 20 °C (monohydrate)
Acidity (pKa)	COOH: 4.5, OH: 10.
Hazards
MSDS	External MSDS
Main hazards	Irritant
Related compounds
Related compounds	Benzoic acid, Phenol, Pyrogallol
	(what is this?) (verify); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants.^[1] The chemical formula is C₆H₂(OH)₃COOH. Gallic acid is found both free and as part of tannins. Salts and esters of gallic acid are termed gallates. Despite its name, it does not contain gallium.

Gallic acid is commonly used in the pharmaceutical industry.^[2] 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.^[3] Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline.^[4]

Gallic acid seems to have anti-fungal and anti-viral properties. Gallic acid acts as a antioxidant and helps to protect our cells against oxidative damage. Gallic acid was found to show cytotoxicity against cancer cells, without harming healthy cells. Gallic acid is used as a remote astringent in cases of internal haemorrhage. Gallic acid is also used to treat albuminuria and diabetes. Some ointment to treat psoriasis and external haemorrhoids contain gallic acid.^[5]

[edit] Historical context and uses

Gallic acid was one of the substances used by Angelo Mai (1782–1854) among other early investigators of palimpsests to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand," often damaging manuscripts for future study.^{[citation needed]}

It has been discovered by French chemist and pharmacist Henri Braconnot (1780-1855) in 1818 and studied by French chemist Théophile-Jules Pelouze (1807-1867).

Early photographers also used it, Joseph Bancroft Reade (1801-1870) for instance and William Fox Talbot (1800-1877) for developing latent images in calotypes. It has also been used as a coating agent in zincography.

[edit] List of plants/foods that contain the chemical

Areca nut
Bearberry (Arctostaphylos sp)
Bergenia sp
Blackberry
Hot chocolate
Drosera (sundew)
Juglans regia (Common walnut)
Mango in peels and leaves
Phyllanthus emblica (Indian gooseberry) in fruits
Raspberry
Syzygium aromaticum (clove)^[6]
Rhodiola rosea (Golden root)
Triphala (Ayurvedic herbal rasayana formula)
Witch hazel (Hamamelis virginiana)
White tea

[edit] Spectral datas

UV-Vis
Retention time
Lambda-max:	220, 271 nm (ethanol)
Extinction coefficient (log ε)
IR
Major absorption bands	ν : 3491, 3377, 1703, 1617, 1539, 1453, 1254 cm⁻¹ (KBr)
NMR
Proton NMR (acetone-d6): d : doublet, dd : doublet of doublets, m : multiplet, s : singlet	δ : 7.15 (2H, s, H-3 and H-7)
Carbon-13 NMR (acetone-d6):	δ : 167.39 (C-1), 144.94 (C-4 and C-6), 137.77 (C-5), 120.81 (C-2), 109.14 (C-3 and C-7)
Other NMR data
MS
Masses of main fragments	ESI-MS [M-H]- m/z : 169.0137

Reference^[7]

[edit] Esters

[edit] Metabolism

Gallate 1-beta-glucosyltransferase uses UDP-glucose and gallate, whereas its two products are UDP and 1-galloyl-beta-D-glucose.

[edit] See also

[edit] References

^ LD Reynolds and NG Wilson, “Scribes and Scholars” 3rd Ed. Oxford: 1991. pp193–4.
^ S. M. Fiuza. "Phenolic acid derivatives with potential anticancer properties––a structure–activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids". Elsevier. http://dx.doi.org/10.1016/j.bmc.2004.04.026.
^ Andrew Waterhouse. "Folin-Ciocalteau Micro Method for Total Phenol in Wine". UC Davis. http://waterhouse.ucdavis.edu/phenol/folinmicro.htm.
^ Tsao, Makepeasce (July 1951). "A New Synthesis Of Mescaline". Journal of the American Chemical Society 73 (11): 5495–5496. ISSN 0002-7863.
^ phytochemicals.info
^ Pathak, S. B. et al. (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.
^ Antimicrobial gallic acid from Caesalpinia mimosoides Lamk. Anchana Chanwitheesuk, Aphiwat Teerawutgulrag, Jeremy D. Kilburn and Nuansri Rakariyatham, Food Chemistry, Volume 100, Issue 3, 2007, Pages 1044-1048

[edit] External links

King's American Dispensatory (1898) entry on Gallic acid

[0] LD Reynolds and NG Wilson, “Scribes and Scholars” 3rd Ed. Oxford: 1991. pp193–4.

[1] S. M. Fiuza. "Phenolic acid derivatives with potential anticancer properties––a structure–activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids". Elsevier. http://dx.doi.org/10.1016/j.bmc.2004.04.026.

[2] Andrew Waterhouse. "Folin-Ciocalteau Micro Method for Total Phenol in Wine". UC Davis. http://waterhouse.ucdavis.edu/phenol/folinmicro.htm.

[3] Tsao, Makepeasce (July 1951). "A New Synthesis Of Mescaline". Journal of the American Chemical Society 73 (11): 5495–5496. ISSN 0002-7863.

[4] ytochemicals.info

[tdmq-5] Pathak, S. B. et al. (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.

[6] Antimicrobial gallic acid from Caesalpinia mimosoides Lamk. Anchana Chanwitheesuk, Aphiwat Teerawutgulrag, Jeremy D. Kilburn and Nuansri Rakariyatham, Food Chemistry, Volume 100, Issue 3, 2007, Pages 1044-1048

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