GALLIC ACID
Gallic acid, a naturally occurring phenolic compound with the chemical formula C7H6O5, is known for its potent antioxidant capabilities, which help neutralize free radicals and mitigate oxidative stress, making it valuable in health, cosmetic, and pharmaceutical applications.
In addition to its antioxidant properties, gallic acid exhibits significant antimicrobial and anti-inflammatory effects, demonstrating its potential in preventing infections and reducing inflammation, and it has shown promise in inhibiting cancer cell growth.
Gallic acid is found in various natural sources such as fruits, tea, oak bark, and certain herbs, and it has historically been used in iron gall ink; today, it is increasingly recognized for its potential health benefits and versatility in diverse industries.
CAS Number: 149-91-7
EC Number: 205-749-9
Molecular Formula: C6h2(Oh)3cooh
Molecular Weight: 170.12
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)
Gallic acid is a naturally occurring phenolic compound known for its diverse range of beneficial properties.
With the chemical formula C7H6O5, Gallic acid features a trihydroxybenzene ring structure that grants it potent antioxidant capabilities, helping to neutralize free radicals and mitigate oxidative stress.
This antioxidant activity plays a crucial role in protecting cells and tissues from damage, making Gallic acid valuable in both health and cosmetic applications.
In addition to Gallic acid's antioxidant effects, Gallic acid exhibits significant antimicrobial properties, demonstrating efficacy against various bacteria and fungi, which underscores its potential in preventing infections.
Gallic acid's anti-inflammatory effects contribute to reducing inflammation and alleviating related symptoms, while its promising anti-cancer potential is highlighted by research showing its ability to inhibit cancer cell growth and induce apoptosis.
Gallic acid is soluble in water and organic solvents, enhancing its versatility for use in pharmaceuticals, skincare products, and traditional medicine.
Commonly found in natural sources such as fruits (grapes and berries), tea, oak bark, and certain herbs, Gallic acid is increasingly utilized in cosmetic formulations for its ability to improve skin health, reduce signs of aging, and offer protection against environmental damage.
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 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 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 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.
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.
Gallic 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.
Uses of Gallic Acid:
Gallic acid is widely utilized across various industries due to its diverse range of beneficial properties.
In the pharmaceutical and medical fields, Gallic acid is valued for its strong antioxidant activity, which helps combat oxidative stress and may contribute to the prevention of chronic diseases and aging.
Gallic acid's antimicrobial and anti-inflammatory properties make it useful in developing treatments for infections and inflammatory conditions.
In the realm of cosmetics, Gallic acid is employed in skincare products for its ability to neutralize free radicals, reduce signs of aging, and enhance skin health.
Additionally, Gallic acid is used as a natural preservative due to its antimicrobial effects, extending the shelf life of products.
In the food and beverage industry, Gallic acid serves as a stabilizing agent and flavor enhancer.
Gallic acid is also important in traditional medicine, where it has been used in various cultures for its purported health benefits.
Gallic acid's role in research and industry underscores its versatility and effectiveness across multiple applications.
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.
Food Sources:
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.
Benefits of Gallic Acid:
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:
Gallic acid is used an astringent.
Gallic acid is used a cyclooxygenase 2 inhibitor.
Gallic acid is used a plant metabolite.
Gallic acid is used an antioxidant.
Gallic acid is used an antineoplastic agent.
Gallic acid is used a human xenobiotic metabolite.
Gallic acid is used an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor.
Gallic acid is used an apoptosis inducer.
Gallic acid is used a geroprotector.
Occurrence of Gallic Acid:
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 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.
Handling and Storage of Gallic Acid:
Handling:
Handle Gallic acid with care, avoiding inhalation and direct contact with skin and eyes.
Use appropriate personal protective equipment (PPE), such as gloves and safety goggles.
Work in a well-ventilated area or fume hood to minimize inhalation risk.
Storage:
Store Gallic acid in a cool, dry place away from moisture and direct sunlight.
Keep the container tightly closed and store it in a labeled, secure container.
Ensure that storage areas are well-ventilated.
Stability and Reactivity of Gallic Acid:
Stability:
Gallic acid is generally stable under recommended storage conditions.
Avoid exposure to light, moisture, and high temperatures to prevent degradation.
Reactivity:
Gallic acid may react with strong oxidizing agents.
Avoid contact with strong acids and bases.
First Aid Measures of Gallic Acid:
Inhalation:
Move the person to fresh air immediately.
If breathing is difficult, seek medical attention.
Skin Contact:
Wash the affected area with soap and water.
Remove contaminated clothing and seek medical advice if irritation persists.
Eye Contact:
Rinse eyes with plenty of water for at least 15 minutes.
Seek medical attention immediately.
Ingestion:
Rinse the mouth with water and drink plenty of water.
Do not induce vomiting unless directed by a medical professional.
Seek medical attention promptly.
Fire Fighting Measures of Gallic Acid:
Extinguishing Media:
Use water spray, foam, dry chemical, or carbon dioxide (CO2) to extinguish fires involving Gallic acid.
Special Hazards:
During a fire, smoke may contain hazardous combustion products.
Wear self-contained breathing apparatus (SCBA) and protective clothing.
Fire Fighting Procedures:
Evacuate the area and ensure proper ventilation.
Approach from upwind and use appropriate fire-fighting techniques.
Accidental Release Measures of Gallic Acid:
Personal Precautions:
Wear appropriate PPE, including gloves, goggles, and protective clothing.
Environmental Precautions:
Prevent spill from entering waterways or drains.
Contain and clean up spills promptly.
Cleanup Methods:
Collect the spilled material using appropriate tools and dispose of it according to local regulations.
Clean the affected area thoroughly with water and detergent.
Exposure Controls/Personal Protective Equipment of Gallic Acid:
Exposure Limits:
Refer to relevant safety data sheets (SDS) for specific exposure limits.
Engineering Controls:
Use local exhaust ventilation or fume hoods to minimize exposure.
PPE:
Respiratory Protection:
Use a respirator if ventilation is inadequate.
Hand Protection:
Wear chemical-resistant gloves.
Eye Protection:
Use safety goggles or face shields.
Skin Protection:
Wear protective clothing to avoid skin contact.
Identifiers of Gallic Acid:
Chemical Formula: C7H6O5
IUPAC Name: 3,4,5-Trihydroxybenzoic acid
CAS Number: 149-91-7
Molecular Weight: 170.12 g/mol
SMILES Notation: C1=CC(=C(C(=C1O)O)O)C(=O)O
InChI Key: UHSKDJGZJHMPON-UHFFFAOYSA-N
PubChem CID: 370
EC Number: 205-464-6
Systematic Name: 3,4,5-Trihydroxybenzoic acid
Chemical Structure:
SMILES: C1=CC(=C(C(=C1O)O)O)C(=O)O
InChI: InChI=1S/C7H6O5/c8-4-1-2-5(10)6(11)3-7(4)9/h1-3,8-11H
Melting Point: 256-258°C (482-496°F)
Boiling Point: Decomposes before boiling
Solubility:
Soluble in water
Soluble in ethanol, acetone, and other organic solvents
Density: Approximately 1.64 g/cm³
Appearance: White to pale yellow crystalline powder
Properties of Gallic Acid:
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
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 5
Rotatable Bond Count: 1
Heavy Atom Count: 12
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
Specifications of Gallic Acid:
Purity:
Minimum Purity: ≥ 98% (by HPLC or other methods)
Assay: The percentage of Gallic acid in the sample, typically ≥ 98%
Appearance:
Form: White to pale yellow crystalline powder
Odor: Odorless or faintly aromatic
Physical Properties:
Melting Point: 256-258°C (482-496°F)
Solubility: Soluble in water, ethanol, acetone, and other organic solvents
Density: Approximately 1.64 g/cm³
Chemical Properties:
Chemical Formula: C7H6O5
Molecular Weight: 170.12 g/mol
pH (1% solution): Typically between 2.5-3.5
