Epigallocatechin

Base Information

• Chemical Name: Epigallocatechin
• CAS No.: 970-74-1
• Deprecated CAS: 98032-84-9,2545-09-7
• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.272
• Hs Code.: 29329990
• European Community (EC) Number: 619-254-4
• NSC Number: 674039
• UNII: 7Z197MG6QL
• DSSTox Substance ID: DTXSID40891550
• Nikkaji Number: J277.681B
• Wikidata: Q51617505
• NCI Thesaurus Code: C68453
• Metabolomics Workbench ID: 21834
• ChEMBL ID: CHEMBL47386
• Mol file: 970-74-1.mol

Synonyms:epigallocatechin;epigallocatechol;gallocatechin;gallocatechol;gallocatechol, (2R-cis)-isomer;gallocatechol, (2R-trans)-isomer;gallocatechol, (2S-trans)-isomer

Chemical Property of Epigallocatechin

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 9.69E-20mmHg at 25°C
• Melting Point: 208-210 °C
• Refractive Index: 1.775
• Boiling Point: 685.6 °C at 760 mmHg
• PKA: 9.02±0.15(Predicted)
• Flash Point: 368.5 °C
• PSA: 130.61000
• Density: 1.695 g/cm³
• LogP: 1.25170
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 306.07395278
• Heavy Atom Count: 22
• Complexity: 380

Purity/Quality:

99% ^*data from raw suppliers

(-)-Epigallocatechin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
• Recent ClinicalTrials: The Role of Tea Catechins and Caffeine in Relation to Energy Metabolism
• Recent NIPH Clinical Trials: Role of Epigallocatechin for the Prevention of Infections in Patients Treated with ImmunoSuppressive Therapy
• Uses: antineoplastic A natural constituent of green tea. It is an antioxidant and a potential cancer chemopreventive agent. An epimer of (-)-Gallocatechin (G188990). A natural product from green tea that induces apoptosis

Technology Process of Epigallocatechin

There total 48 articles about Epigallocatechin 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: 95.0%

(-)-epigallocathechin gallate (2596-50-1,4233-96-9,5127-64-0,19065-20-4,107965-88-8,137766-94-0,989-51-5) → epigallocatechin (970-73-0,1617-55-6,3371-27-5,13425-13-3,136892-45-0,970-74-1,98032-84-9)

Guidance literature:

With tannase; In water; at 35 ℃; for 12h; Enzymatic reaction;

DOI:10.1016/j.tetlet.2020.151601

Reference yield: 72.0%

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol (332386-74-0) → epigallocatechin (970-73-0,1617-55-6,3371-27-5,13425-13-3,136892-45-0,970-74-1,98032-84-9)

Guidance literature:

With 20% palladium hydroxide on carbon; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 5h;

DOI:10.1039/c003464a

Reference yield: 51.0%

C30H38O10 (1449477-39-7) → epigallocatechin (970-73-0,1617-55-6,3371-27-5,13425-13-3,136892-45-0,970-74-1,98032-84-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/asia.201201168

upstream raw materials:

(2R,2''R,3S,3''R,4S)-[4,8]-2,3-trans-3,4-trans-(+)-catechin-(-)-epigallocatechin

(-)-epigallocatechin 3,4'-di-O-gallate

(-)-epigallocatechin 3,3'-di-O-gallate

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate

Downstream raw materials:

2,2-diphenyl-1-picrylhydrazine

theaflavin

theanaphthoquinone

S-(5'-adenosyl)-L-homocysteine

Refernces

• 1、 Hirose, Sayumi,Kamatari, Yuji O.,Yanase, Emiko. "Mechanism of oolongtheanin formation via three intermediates". supporting information. . Retrieved 2020/01/24.
• 2、 Lin, Guang,Chang, Le,Liu, Yongxiang,Xiang, Zheng,Chen, Jiahua,Yang, Zhen. "Enantioselective total syntheses of (+)-gallocatechin, (-)- epigallocatechin, and 8-C-ascorbyl-(-)-epigallocatechin". . p. 700 - 704. Retrieved 2013/05/09.