Gallotannin

Base Information

• Chemical Name: Gallotannin
• CAS No.: 1401-55-4
• Deprecated CAS: 1041198-33-7,1041198-44-0,2322285-95-8,61790-06-5,67167-65-1,73891-88-0,93615-37-3,1201816-48-9,88196-66-1
• Molecular Formula: C76H52O46
• Molecular Weight: 1701.28
• Hs Code.: 32019090
• European Community (EC) Number: 215-753-2,226-562-9
• ChEMBL ID: CHEMBL506247
• DSSTox Substance ID: DTXSID00892987
• NCI Thesaurus Code: C66579
• Nikkaji Number: J218.007C
• RXCUI: 10328
• Wikidata: Q427956
• Mol file: 1401-55-4.mol

Synonyms:(2S,3R,4S,5R,6R)-3,4,5-tris(3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy)-6-((3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy)methyl)oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate;Gallotannic Acid;Gallotannin;Tannic Acid

Chemical Property of Gallotannin

Chemical Property:

• Appearance/Colour: light yellow to tan solid with a faint odor
• Melting Point: 218 °C(lit.)
• Refractive Index: 1.927
• Boiling Point: 862.78°C (rough estimate)
• Flash Point: 198 °C
• PSA: 777.98000
• Density: 2.12 g/cm³
• LogP: 4.83810
• Storage Temp.: Storage temperature: no restrictions.
• Sensitive.: Air & Light Sensitive
• Solubility.: ethanol: soluble100mg/mL, yellow to brown
• Water Solubility.: 250 g/L (20 ºC)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 25
• Hydrogen Bond Acceptor Count: 46
• Rotatable Bond Count: 31
• Exact Mass: 1700.1729741
• Heavy Atom Count: 122
• Complexity: 3570

Purity/Quality:

81% 93% ^*data from raw suppliers

Tannic Acid ACS ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 40-62-63-68-36/37/38-52/53
• Safety Statements: 24/25-36-26-36/37/39-22-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)OCC3C(C(C(C(O3)OC(=O)C4=CC(=C(C(=C4)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)OC(=O)C9=CC(=C(C(=C9)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O
• Isomeric SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)C4=CC(=C(C(=C4)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)OC(=O)C9=CC(=C(C(=C9)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O
• Recent ClinicalTrials: Evaluation of Topical Lidocaine Spray as Adjuvant to Upper Gastrointestinal Endoscopy in Children
• Description: Gallotannin, also known as Tannic acid, is a primary gallo-tannin derived from hydrolysable tannins found in gall nuts and various plant sources. It possesses weak acidic properties and a strong astringent taste. Gallotannin exhibits a wide range of medicinal benefits, including anticancer, antioxidant, anti-inflammatory, and neuroprotective effects. Its hydroxy and carboxy groups enable interactions with biopolymers and macromolecules, making it a promising pharmaceutical candidate for various applications.^[1]
• Used in Anticancer Applications: Gallotannin is employed as an anticancer agent, particularly against solid malignancies such as liver, breast, lung, pancreatic, colorectal, and ovarian cancers. It modulates several oncological signaling pathways, including JAK/STAT, RAS/RAF/mTOR, TGF-β1/TGF-β1R, VEGF/VEGFR, and CXCL12/CXCR4 axes, exerting inhibitory effects on tumor growth and progression.^[2],^[3] Additionally, it demonstrates synergistic anticancer effects when combined with conventional chemotherapeutic drugs, enhancing chemo-sensitivity and efficacy in resistant cases. Despite its promising anticancer properties, the clinical applications of gallotannin have been limited by challenges such as poor lipid solubility, low bioavailability, off-taste, and short half-life.^[1]
• Recent development in drug delivery system: To overcome the limitations of gallotannin, novel drug delivery systems have been developed to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for gallotannin delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes. These drug delivery systems enable targeted and controlled release of gallotannin, thereby enhancing its anticancer effects while minimizing adverse effects. Such advancements in drug delivery technology hold promise for promoting the clinical development and utilization of gallotannin as an effective anticancer therapy.^[1]
• Production Methods: Gallotannin is obtained through extraction from plant sources or by chemical synthesis methods. Techniques such as HPLC, column chromatography, and high-speed counter-current chromatography can be employed to recover gallotannin with high purity.
• References: [1] Recent Advances in Tannic Acid (Gallotannin) Anticancer Activities and Drug Delivery Systems for Efficacy Improvement; A Comprehensive Review; (DOI 10.3390/molecules26051486); [2] Cell Death by Gallotannin Is Associated with Inhibition of the JAK/STAT Pathway in Human Colon Cancer Cells; (DOI 10.1016/j.curtheres.2020.100589); [3] Inhibitory Effect of Gallotannin on Lung Metastasis of Metastatic Colorectal Cancer Cells by Inducing Apoptosis, Cell Cycle Arrest and Autophagy; (DOI 10.1142/S0192415X21500725)