Gallic Acid

• CAS: 149-91-7
• Catalog Number: ACM149917-1
• Category: Main Products
• Molecular Weight: 170.12
• Molecular Formula: C7H6O5
• Description: BETZ 0276 is a trihydroxybenzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3COOH. BETZ 0276 is found both free and as part of hydrolyzable tannins. The BETZ 0276 groups are usually bonded to form dimers such as ellagic acid. Hydrolyzable tannins break down on hydrolysis to give BETZ 0276 and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins respectively.BETZ 0276 forms intermolecular esters (depsides) such as digallic and triBETZ 0276, and cyclic ether-esters (depsidones).
• Synonyms: Graphite oxide
• IUPAC Name: 3,4,5-Trihydroxybenzoic acid
• Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)O
• InChI: InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
• InChI Key: LNTHITQWFMADLM-UHFFFAOYSA-N
• Boiling Point: 259.73 °C
• Melting Point: 251 °C(lit.)
• Flash Point: 271 °C
• Density: 1.694 g/cm³
• Solubility: Soluble in oxygenated solvents
• Appearance: Off-white powder
• Storage: 2-8 °C
• Complexity: 169
• EC Number: 205-749-9
• Exact Mass: 170.02152329
• Hazard Codes: Xi
• HS Code: 2918290000
• LogP: 0.50160
• MDL Number: MFCD00002510
• Monoisotopic Mass: 170.02152329
• pKa: 4.41(at 25 °C)
• PSA: 97.99
• Refractive Index: 1.5690
• Solubility In Water: 12 g/L
• Stability: Stability Stable, but may discolour upon exposure to light. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, acid chlorides, acid anhydrides.
• Storage Conditions: Do not store in direct sunlight. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from light.
• Topological Polar Surface Area: 98 Ų
• Vapor Pressure: 7.32E-11mmHg at 25°C
• WGK Germany: 2

Case Study

Pharmacological Effects of Gallic Acid in Health and Disease

Kahkeshani, Niloofar, et al. Iranian journal of basic medical sciences, 2019, 22(3), 225.

Gallic acid (3,4,5-trihydroxybenzoic acid) is a naturally occurring low molecular weight triphenolic compound. This review outlines the pharmacological and biological activities of gallic acid based on in vitro studies and animal models, aiming to clarify the pharmacological profile of this compound. Current research demonstrates that gallic acid offers various beneficial effects, including antioxidant, anti-inflammatory, and antitumor properties. Furthermore, it has been linked to therapeutic outcomes in gastrointestinal, neuropsychological, metabolic, and cardiovascular diseases.
Brief summary of the therapeutic effects of gallic acid
· Antibacterial activity: Gallic acid inhibits the motility, adhesion, and biofilm formation of several bacteria, including Pseudomonas aeruginosa, Staphylococcus aureus, Streptococcus mutans, Chromobacterium violaceum, and Listeria monocytogenes.
· Anticancer activity: Gallic acid exhibits cytotoxic and antitumor effects by modulating the antioxidant/prooxidant balance. It can also induce cell cycle arrest, autophagy, and apoptosis by activating the caspase pathway and generating reactive oxygen species (ROS).
· Gastrointestinal diseases: Gallic acid protects the gastrointestinal mucosa from ulcers through various mechanisms, such as reducing acid secretion, promoting the release of endogenous antioxidants and protective factors (including SOD, CAT, endothelial nitric oxide synthase (e-NOS), and prostaglandin E2 (PGE2)), and decreasing oxidative stress and lipid peroxidation.
· Cardiovascular diseases: Pre-treatment with gallic acid has been shown to mitigate the damaging oxidative effects associated with myocardial infarction by enhancing the activity of antioxidant enzymes and increasing levels of non-enzymatic antioxidants.

Synthetic Use

Upstream Synthesis Route 1

• 71-23-8
• 99-24-1

• 121-79-9
• 149-91-7

Reference: [1] Food Chemistry, 2011, vol. 128, # 1, p. 214 - 217

Downstream Synthesis Route 1

• 71-23-8
• 149-91-7

• 121-79-9

Reference: [1] Patent: CN105294433, 2016, A, . Location in patent: Paragraph 0028

Downstream Synthesis Route 2

• 149-91-7
• 71-36-3

• 121-79-9

Reference: [1] Patent: US4613683, 1986, A,

Downstream Synthesis Route 3

• 71-23-8
• 149-91-7

• 121-79-9

Reference: [1]Patent: CN105294433,2016,A .Location in patent: Paragraph 0028

Downstream Synthesis Route 4

• 111-87-5
• 149-91-7

• 1034-01-1

Reference: [1]European Journal of Medicinal Chemistry,2015,vol. 92,p. 656 - 671

Downstream Synthesis Route 5

• 112-53-8
• 149-91-7

• 1166-52-5

Reference: [1]European Journal of Medicinal Chemistry,2015,vol. 92,p. 656 - 671

* For details of the synthesis route, please refer to the original source to ensure accuracy.