Epigallocatechin Gallate

Base Information

• Chemical Name: Epigallocatechin Gallate
• CAS No.: 989-51-5
• Deprecated CAS: 863-65-0
• Molecular Formula: C₂₂H₁₈O₁₁
• Molecular Weight: 458.378
• Hs Code.: 29339900
• European Community (EC) Number: 479-560-7,619-381-5
• UNII: BQM438CTEL
• DSSTox Substance ID: DTXSID1029889
• Nikkaji Number: J134.058A
• Wikipedia: Epigallocatechin_gallate
• Wikidata: Q393339
• NCI Thesaurus Code: C1088
• RXCUI: 24246
• Pharos Ligand ID: 8G955XN2LS69
• Metabolomics Workbench ID: 22118
• ChEMBL ID: CHEMBL297453
• Mol file: 989-51-5.mol

Synonyms:EGCG cpd;epigallo-catechin gallate;epigallocatechin gallate;epigallocatechin-3-gallate;epigallocatechin-3-O-gallate

Chemical Property of Epigallocatechin Gallate

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 3.71E-35mmHg at 25°C
• Melting Point: 222-224 °C
• Refractive Index: -175.5 ° (C=1, EtOH)
• Boiling Point: 909.1 °C at 760 mmHg
• PKA: 7.75±0.25(Predicted)
• Flash Point: 320 °C
• PSA: 197.37000
• Density: 1.9 g/cm³
• LogP: 2.23320
• Storage Temp.: 2-8°C
• Solubility.: H2O: ≥5mg/mL, clear
• Water Solubility.: Soluble in ethanol, dimethyl formamide, water.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 458.08491139
• Heavy Atom Count: 33
• Complexity: 667

Purity/Quality:

98%, ^*data from raw suppliers

EGCG ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• Isomeric SMILES: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• Recent ClinicalTrials: Oxygen Atomizing Inhalation of EGCG in the Treatment Interstitial Pneumonia in Cancer Patients
• Recent EU Clinical Trials: Topical sinecatechins ointment in treatment of primary superficial Basal Cell Carcinoma: a double blind, randomized, placebo-controlled trial.
• Uses: (-)-Epigallocatechin Gallate is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-? and amaloid plaques in mice. This compound has neuroprotective properties. telomerase inhibitor An inhibitor of Bcl-2 and NOS2 (-)-Epigallocatechin Gallate is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-β and amaloid plaques in mice. This compound has neuroprotective properties. A tumor-inhibiting constituent of green tea. Alters the cleavage of amyloid precursor protein, decreasing production of amaloid- and amaloid plaques in mice

Technology Process of Epigallocatechin Gallate

There total 49 articles about Epigallocatechin Gallate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.6%

(-)-epigallocatechin 3-O-galloylperacetate (148707-39-5) → (-)-epigallocathechin gallate (2596-50-1,4233-96-9,5127-64-0,19065-20-4,107965-88-8,137766-94-0,989-51-5)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 4h; Cooling with ice;

DOI:10.1080/00397911.2011.585269

Reference yield: 91.0%

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (332386-77-3) → (-)-epigallocathechin gallate (2596-50-1,4233-96-9,5127-64-0,19065-20-4,107965-88-8,137766-94-0,989-51-5)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

DOI:10.1021/ol000394z

Reference yield: 29.2%

1,2-diamino-benzene (95-54-5) + EGCg quinone dimer A (225793-49-7) → (-)-epigallocathechin gallate (2596-50-1,4233-96-9,5127-64-0,19065-20-4,107965-88-8,137766-94-0,989-51-5) + 3,4,5-Trihydroxy-benzoic acid (2R,3R)-5,7-dihydroxy-2-(4-hydroxy-phenazin-2-yl)-chroman-3-yl ester

Guidance literature:

With acetic acid; In ethanol; at 80 ℃; for 2.5h;

DOI:10.1016/j.tet.2003.08.025

upstream raw materials:

assamicain C

assamicain A

assamicain B

epicatechin 3-O-gallate-(4β->6)-epigallocatechin 3-O-gallate

Downstream raw materials:

2,2-diphenyl-1-picrylhydrazine

purpurogallin-4-carboxylic acid

epitheaflagallin 3-O-gallate

oolongtheanine

Refernces

• 1、 Wang, Yu-Na,Wang, Jing,Yang, Hao-Nan,Zhang, Bang-Lei,Zhang, Pan,Sun, Pei-Yuan,Zhang, Nin,Wang, Ya,Sheng, Jun,Wang, Xuan-Jun,Zi, Cheng-Ting. "The oxidation of (-)-epigallocatechin-3-gallate inhibits T-cell acute lymphoblastic leukemia cell line HPB-ALL: Via the regulation of Notch1 expression". . p. 1679 - 1684. Retrieved 2020/01/28.
• 2、 Sakakibara, Takumi,Sawada, Yoshiharu,Wang, Jilite,Nagaoka, Satoshi,Yanase, Emiko. "Molecular Mechanism by Which Tea Catechins Decrease the Micellar Solubility of Cholesterol". . . Retrieved 2019/07/03.