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GALLIC ACID

CAS NUMBER: 149-91-7

EC NUMBER: 205-749-9

MOLECULAR FORMULA: C6H2(OH)3COOH

MOLECULAR WEIGHT: 170.12

IUPAC NAME: 3,4,5-trihydroxybenzoic acid

 

Isolation and Derivatives:
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.

Biosynthesis:
Chemical structure of 3,5-didehydroshikimate
Gallic Acid is formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. 
This latter compound aromatizes.

Reactions:
*Oxidation and oxidative coupling:
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.
Gallic Acid forms intermolecular esters (depsides) such as digallic and cyclic ether-esters (depsidones).

*Hydrogenation
Hydrogenation of Gallic Acid gives the cyclohexane derivative hexahydroGallic Acid.

*Decarboxylation
Heating Gallic Acid gives pyrogallol (1,2,3-trihydroxybenzene). 
This conversion is catalyzed by gallate decarboxylase.

*Esterification
Many esters of Gallic Acid are known, both synthetic and natural. 
Gallate 1-beta-glucosyltransferase catalyzes the glycosylation (attachment of glucose) of Gallic Acid.

Historical Context and Uses:
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 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. 
Gallic Acid could then be mixed with green vitriol (ferrous sulfate) — obtained by allowing sulfate-saturated water from a spring or mine drainage to evaporate — and gum arabic from acacia trees; this combination of ingredients produced the ink.

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.

Gallic Acid was first studied by the Swedish chemist Carl Wilhelm Scheele in 1786.
In 1818, French chemist and pharmacist Henri Braconnot (1780–1855) devised a simpler method of purifying Gallic Acid from galls; Gallic Acid was also studied by the French chemist Théophile-Jules Pelouze (1807–1867), among others.

Occurrence:
The 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 found in a number of land plants, such as the parasitic plant Cynomorium coccineum, the aquatic plant Myriophyllum spicatum, and the blue-green alga Microcystis aeruginosa.
Gallic Acid is also found in various oak species, Caesalpinia mimosoides, and in the stem bark of Boswellia dalzielii, among others. 

Many foodstuffs contain various amounts of Gallic Acid, especially fruits (including strawberries, grapes, bananas), as well as teas, cloves, and vinegars.
Carob fruit is a rich source of Gallic Acid (24–165 mg per 100 g).

Gallic Acid (GA) is a member of the hydroxybenzoic acids found in methyl acetate fraction and hydroalcoholic extract from Schinus terebinthifolius leaves
Gallic Acid is the most popular of trihydroxybenzoic acids. 

Gallic Acid is also known as 3,4,5-trihydroxybenzoic acid, Gallic Acid has been reported in most plants.
Gallic Acid is a type of phenolic acid which is found in tea leaves and some fruits. 

Gallic Acid is typically used in Chinese herbal medicine. 
Gallic Acid was shown to have positive effects on hypertension, vascular calcification, cardiac remodeling, and fibrosis 

Gallic Acid, also known as 3, 4, 5-trihydroxybenzoic acid, C6H2 (OH)3 COOH chemical structure.
Gallic Acid has a molecular weight of 170.12 g/mol, is a monomeric phenolic compound solid, and colorless, which is bound to sugars and belong to group of hydrolysable tannins.

Gallic Acid can be found in plant material as free acid, esters, catechin derivatives, and hydrolysable tannins. 
Gallic Acid is present in relatively high concentrations in a number of vegetal samples and in industrial wastes from where it could be extracted

Gallic Acid is a phenolic acid, or bioactive compound, found in plants. 
Gallic Acid has antioxidant properties and may offer other health benefits.

What is Gallic Acid?
Gallic Acid (also known as 3,4,5-trihydroxybenzoic acid) is an antioxidant and phenolic acid found in most plants in various amounts.

Gallic Acid was used from the 12th to 19th centuries as a major component of iron gall ink, the standard writing ink in Europe. 
Today, it’s becoming more recognized for its potential health benefits.

Food Sources of Gallic Acid:
Gallic Acid is naturally found in a variety of plants — particularly in the bark of oak species and Boswellia dalzielii, an African tree.
What’s more helpful to most people is understanding which common foods provide it. 

Some of the best food sources of Gallic Acid include:
-strawberry
-grape
-banana
-blueberry
-apple
-walnut
-cashew
-hazelnut
-red wine
-green tea
-avocado
-blackcurrant
-guava
-mango
-mulberry
-pomegranate

Gallic Acid is an antioxidant and phenolic compound found in many plants. 
Foods like nuts, berries, and other fruits that you may already include in your diet are good sources.

Potential Benefits:
While more research is needed to determine the potential health benefits of Gallic Acid, current studies suggest that it may offer antimicrobial, anti-obesity, and antioxidant properties that could improve cancer and brain health.

Gallic Acid is an odorless white solid. 
Gallic Acid sinks in water.

Gallic Acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. 
Gallic Acid has a role as: 

-an astringent

-a cyclooxygenase 2 inhibitor

-a plant metabolite

-an antioxidant

-an antineoplastic agent

-a human xenobiotic metabolite

-an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor

-an apoptosis inducer

-a geroprotector


Gallic Acid is a conjugate acid of a gallate.
Gallic Acid is a natural product found in Cunonia macrophylla, Sedum sediforme, and other organisms with data available.

Gallic Acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6H2(OH)3CO2H. 
Gallic Acid is classified as a phenolic acid. 

Gallic Acid is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. 
Gallic Acid is a white solid, although samples are typically brown owing to partial oxidation. 
Salts and esters of Gallic Acid are termed "gallates".


PHYSICAL PROPERTIES:

-Molecular Weight: 170.12    

-XLogP3: 0.7    

-Exact Mass: 170.02152329    

-Monoisotopic Mass: 170.02152329    

-Topological Polar Surface Area: 98 Ų    

-Physical Description: Gallic Acid is an odorless white solid

-Color: Colorless or slightly yellow

-Form: cyrstalline needles or prisms.

-Boiling Point: SUBLIMES

-Solubility: 0.07 M

-Density: 1.69 kg/l

-LogP: 0.7

-pKa: 4.40

-Collision Cross Section: 130.9 Ų
    

Gallic Acid (also known as 3,4,5-trihydroxybenzoic acid) is an antioxidant and phenolic acid found in most plants in various amounts.
Gallic Acid was used from the 12th to 19th centuries as a major component of iron gall ink, the standard writing ink in Europe. 
Today, Gallic Acid’s becoming more recognized for its potential health benefits.


CHEMICAL PROPERTIES:

-Hydrogen Bond Donor Count: 4    

-Hydrogen Bond Acceptor Count: 5    

-Rotatable Bond Count: 1    

-Heavy Atom Count: 12    

-Formal Charge: 0    

-Complexity: 169    

-Isotope Atom Count: 0    

-Defined Atom Stereocenter Count: 0    

-Undefined Atom Stereocenter Count: 0    

-Defined Bond Stereocenter Count: 0    

-Undefined Bond Stereocenter Count: 0    

-Covalently-Bonded Unit Count: 1    

-Compound Is Canonicalized: Yes

Gallic Acid (GA) is a member of the hydroxybenzoic acids found in methyl acetate fraction and hydroalcoholic extract from Schinus terebinthifolius leaves
Gallic Acid is the most popular of trihydroxybenzoic acids. 
Gallic Acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6H2(OH)3CO2H. 

Gallic Acid is classified as a phenolic acid. 
Gallic Acid is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants.
Gallic Acid is a white solid, although samples are typically brown owing to partial oxidation. 

Salts and esters of Gallic Acid are termed "gallates".
Gallic Acid is a phenolic compound also known as 3,4,5-trihydroxybenzoic acid. 

Gallic Acid is found both as a free state and as a constituent of tannins, namely, gallotannin. 
Gallic Acid and its derivatives are present in nearly every part of the plant, such as bark, wood, leaf, fruit, root, and seed

Gallic Acid is also known as 3,4,5-trihydroxybenzoic acid, Gallic Acid has been reported in most plants.
Gallic Acid is a type of phenolic acid which is found in tea leaves and some fruits. 

Gallic Acid is typically used in Chinese herbal medicine. 
Gallic Acid was shown to have positive effects on hypertension, vascular calcification, cardiac remodeling, and fibrosis 
Gallic Acid, also known as 3, 4, 5-trihydroxybenzoic acid, C6H2 (OH)3 COOH chemical structure.

Gallic Acid has a molecular weight of 170.12 g/mol, is a monomeric phenolic compound solid, and colorless, which is bound to sugars and belong to group of hydrolysable tannins.
Gallic Acid can be found in plant material as free acid, esters, catechin derivatives, and hydrolysable tannins. 

Gallic Acid is present in relatively high concentrations in a number of vegetal samples and in industrial wastes from where it could be extracted
Gallic Acid is a phenolic acid, or bioactive compound, found in plants. 
Gallic Acid has antioxidant properties and may offer other health benefits.


SYNONYMS: 

Gallic Acid
3,4,5-Trihydroxybenzoic acid
gallate
Benzoic acid, 3,4,5-trihydroxy-
Gallic Acid, tech.
Pyrogallol-5-carboxylic acid
Kyselina gallova
3,4,5-Trihydroxybenzoate
Gallic Acid polymer
Gallicum acidum
Kyselina 3,4,5-trihydroxybenzoova
3,4,5-trihydroxy-Benzoic acid
Benzoic acid, 3,4,5-trihydroxy-, homopolymer
Kyselina gallova
gallic-acid
Kyselina 3,4,5-trihydroxybenzoova [Czech]
Gallic Acid, F
GDE
(?)-Gallic Acid
3,4,5-Trihydroxybenzoic acid, anhydrous
SpecPlus_000307
5-Trihydroxybenzoic acid
3,5-Trihydroxybenzoic acid
3,4,5-trihydroxy-Benzoate
Oprea1_087792
3-10-00-02070 (Beilstein Handbook Reference)
3,4,5-Trihydroxybenzoate, X
Benzoic acid,4,5-trihydroxy-
3,4,5-Trihydroxybenzoic acid;
Gallic Acid, puriss., 98.0%
Pharmakon1600-00210369
Gallic Acid, 97.5-102.5% (titration)
3,4,5-trihydroxybenzoic acid (ACD/Name 4.0)
 

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