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
• 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.

Gallic acid's therapeutic and industrial antioxidant applications

Badhani, Bharti, Neha Sharma, and Rita Kakkar. Rsc Advances 5.35 (2015): 27540-27557.

Gallic acid (3,4,5-trihydroxybenzoic acid) is a naturally occurring, low-molecular-weight triphenolic compound that has emerged as a potent antioxidant and potent apoptosis inducer. The bioavailability and biosynthetic pathway of gallic acid have been investigated through various in vitro, in vivo, and in silico studies, providing insights into the triphenolic molecule's mode of action, free radical scavenging activity, ability to inhibit lipid peroxidation, ability to maintain endogenous defenses and metal ion chelation, and the factors contributing to its high antioxidant activity.
Gallic acid is a strong chelator that forms a highly stable complex with Fe(III). Complex formation with Fe(III) results in the oxidation of GA to hydroxyquinone and the simultaneous reduction of Fe(III) to Fe(II). Multiple studies have demonstrated that the complexation process is pH-dependent, starting at pH 3 and continuing to increase in chelation up to pH 9. In a 1:1 complex, iron binds to two adjacent hydroxyl groups of the GA molecule.

Gallic acid's anti-melanin and antioxidant properties

Kim, You-Jung. Biological and Pharmaceutical Bulletin 30.6 (2007): 1052-1055.

In the search for new skin-whitening agents, the melanin production inhibitory effects of gallic acid (GA) have been investigated. In this study, the effects of gallic acid on mushroom tyrosinase, tyrosinase inhibitory activity, and melanin content in B16 melanoma cells (B16 cells) were evaluated. The results showed that gallic acid exhibited potent anti-tyrosinase activity. Furthermore, data on mouse tyrosinase activity and melanin biosynthesis demonstrated that gallic acid effectively inhibited mouse tyrosinase activity and melanin content.
B16 cells were examined by measuring the oxidation rate of α-DOPA. Cells were seeded at a density of 510 cells/ml in 24-well culture dishes. B16 cells were incubated in the presence or absence of 100 nA-MSH and then treated with various concentrations of gallic acid for 24 hours. Cells were lysed in 100 ml of 50% sodium phosphate buffer (pH 6.8) containing 1% Triton X-100 and 0.1 M phenylmethylsulfonyl fluoride and then frozen at 80°C for 30 minutes. After thawing and mixing, the cell extract was clarified by centrifugation at 12,000 g for 30 minutes at 4°C. The supernatant and 20 ml of DOPA were placed in a 96-well plate, and the absorbance at 492 nm was read every 10 minutes for 1 hour at 37°C using an ELISA reader.

The prospect and molecular mechanisms of gallic acid's anticancer activity

Subramanian, A. P., et al. Rsc Advances 5.45 (2015): 35608-35621.

Gallic acid (GA) is one of the phenolic acids found in many dietary substances and herbs used in ancient medicine. It possesses anti-inflammatory, antioxidant, antiviral, and antibacterial properties. Various in vitro and in vivo studies of GA against various cancer cell lines have been reported. Previous studies have shown that GA's anticancer activity is associated with the induction of apoptosis through different mechanisms, such as reactive oxygen species (ROS) production, modulation of apoptotic and anti-apoptotic proteins, inhibition and promotion of oncogenes, inhibition of matrix metalloproteinases (MMPs), and cell cycle arrest, depending on the cancer type studied. Ultimately, GA and its derivatives may be considered as effective monotherapy for cancer treatment or in combination with other anticancer drugs to enhance the efficiency of chemotherapy. The cell death-inducing effects of gallic acid were studied in four human lung cancer cell lines: small cell carcinoma (SBC-3), squamous cell carcinoma (EBC-1), adenocarcinoma (A549), and the cisplatin-resistant subclone SBC-3. GA exhibited a dose-dependent effect on cancer cells. GA treatment resulted in changes in cell morphology, DNA fragmentation, and loss of viability (IC50 values for the cell lines: 10, 20, and 60 μg/ml, respectively). This was further investigated by studying the in vivo antitumor effects of oral administration of gallic acid in C57 black mice transplanted with LL-2 cells. Cells were treated with GA and/or cisplatin. Mice treated with a combination of cisplatin and GA (IC50: 200 μM) exhibited reduced tumor weight compared to cisplatin alone. This suggests that GA could be used in combination with anticancer drugs as an effective treatment for lung cancer.

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.