Names | |||
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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 |
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KEGG | |||
PubChem CID | |||
RTECS number |
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UNII |
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CompTox Dashboard (EPA) | |||
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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 | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | Irritant | ||
NFPA 704 (fire diamond) | |||
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). |
Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C 6 H 2(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.
Gallic acid is easily freed from gallotannins by acidic or alkaline hydrolysis. When heated with concentrated sulfuric acid, gallic acid converts to rufigallol. Hydrolyzable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins, respectively. [2]
Gallic acid is formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound aromatizes. [3] [4]
Alkaline solutions of gallic acid are readily oxidized by air. The oxidation is catalyzed by the enzyme gallate dioxygenase, an enzyme found in Pseudomonas putida .
Oxidative coupling of gallic acid with arsenic acid, permanganate, persulfate, or iodine yields ellagic acid, as does reaction of methyl gallate with iron(III) chloride. [5] Gallic acid forms intermolecular esters (depsides) such as digallic and cyclic ether-esters (depsidones). [5]
Hydrogenation of gallic acid gives the cyclohexane derivative hexahydrogallic acid. [6]
Heating gallic acid gives pyrogallol (1,2,3-trihydroxybenzene). This conversion is catalyzed by gallate decarboxylase.
Many esters of gallic acid are known, both synthetic and natural. Gallate 1-beta-glucosyltransferase catalyzes the glycosylation (attachment of glucose) of gallic acid.
Gallic acid is an important component of iron gall ink, the standard European writing and drawing ink from the 12th to 19th centuries, with a history extending to the Roman empire and the Dead Sea Scrolls. Pliny the Elder (23–79 AD) describes the use of gallic acid as a means of detecting an adulteration of verdigris [7] and writes that it was used to produce dyes. Galls (also known as oak apples) from oak trees were crushed and mixed with water, producing tannic acid. It could then be mixed with green vitriol (ferrous sulfate)—obtained by allowing sulfate-saturated water from a spring or mine drainage to evaporate[ citation needed ]—and gum arabic from acacia trees; this combination of ingredients produced the ink. [8]
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 rendering manuscripts too damaged for subsequent study by other researchers. [9]
Gallic acid was first studied by the Swedish chemist Carl Wilhelm Scheele in 1786. [10] In 1818, French chemist and pharmacist Henri Braconnot (1780–1855) devised a simpler method of purifying gallic acid from galls; [11] gallic acid was also studied by the French chemist Théophile-Jules Pelouze (1807–1867), [12] among others.
When mixed with acetic acid, gallic acid had uses in early types of photography, like the calotype to make the silver more sensitive to light; it was also used in developing photographs. [13]
Gallic acid is found in a number of land plants, such as the parasitic plant Cynomorium coccineum , [14] the aquatic plant Myriophyllum spicatum , and the blue-green alga Microcystis aeruginosa . [15] Gallic acid is also found in various oak species, [16] Caesalpinia mimosoides, [17] and in the stem bark of Boswellia dalzielii, [18] among others. Many foodstuffs contain various amounts of gallic acid, especially fruits (including strawberries, grapes, bananas), [19] [20] as well as teas, [19] [21] cloves, [22] and vinegars. [23] [ clarification needed ] Carob fruit is a rich source of gallic acid (24–165 mg per 100 g). [24]
Also known as galloylated esters:
Gallate esters are antioxidants useful in food preservation, with propyl gallate being the most commonly used. Their use in human health is scantly supported by evidence.
UV-Vis | |
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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
| δ : 7.15 (2H, s, H-3 and H-7) |
Carbon-13 NMR
| δ : 167.39 (C-1), |
Other NMR data | |
MS | |
Masses of main fragments | ESI-MS [M-H]- m/z : 169.0137 ms/ms (iontrap)@35 CE m/z product 125(100), 81(<1) |
Tannins are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids.
Flavan-3-ols are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They play a part in plant defense and are present in the majority of plants.
Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.
Iron gall ink is a purple-black or brown-black ink made from iron salts and tannic acids from vegetable sources. It was the standard ink formulation used in Europe for the 1400-year period between the 5th and 19th centuries, remained in widespread use well into the 20th century, and is still sold today.
Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols.
Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.
Propyl gallate, or 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 oils and fats to prevent oxidation. As a food additive, it is used under the E number E310.
Thearubigins are polymeric polyphenols that are formed during the enzymatic oxidation and condensation of two gallocatechins with the participation of polyphenol oxidases during the fermentation reactions in black tea. Thearubigins are red in colour and are responsible for much of the staining effect of tea. Therefore, a black tea often appears red while a green or white tea has a much clearer appearance. The colour of a black tea, however, is affected by many other factors as well, such as the amount of theaflavins, another oxidized form of polyphenols.
Epigallocatechin gallate (EGCG), also known as epigallocatechin-3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin.
Theaflavin digallate (TFDG) is an antioxidant natural phenol found in black tea, and a theaflavin derivative.
The enzyme tannase (EC 3.1.1.20) catalyzes the following reaction:
Phenolic compounds—natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.
Ethyl 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.
Digallic acid is a polyphenolic compound found in Pistacia lentiscus. Digallic acid is also present in the molecule of tannic acid. Digalloyl esters involve either -meta, or -para depside bonds.
A hydrolysable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.
The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.
Gallocatechin gallate (GCG) is the ester of gallocatechin and gallic acid and a type of catechin. It is an epimer of epigallocatechin gallate (EGCG).
Quercus infectoria or the Aleppo oak is a species of oak well known for producing galls that have been traditionally used for centuries in Asia medicinally while also used in softening leather and in making black dye and ink.
The phenolic content in tea refers to the phenols and polyphenols, natural plant compounds which are found in tea. These chemical compounds affect the flavor and mouthfeel of tea. Polyphenols in tea include catechins, theaflavins, tannins, and flavonoids.