Gallocatechin gallate

Base Information

• Chemical Name: Gallocatechin gallate
• CAS No.: 5127-64-0
• Molecular Formula: C₂₂H₁₈O₁₁
• Molecular Weight: 458.378
• UNII: 0C056HB16M
• ChEMBL ID: CHEMBL126079
• DSSTox Substance ID: DTXSID701336201
• Metabolomics Workbench ID: 21950
• Nikkaji Number: J387.904F
• Pharos Ligand ID: 8G99GWSAXN36
• Wikidata: Q5519120
• Wikipedia: Gallocatechin_gallate
• Mol file: 5127-64-0.mol

Synonyms:gallocatechin gallate;gallocatechin-3-gallate

Chemical Property of Gallocatechin gallate

Chemical Property:

• Melting Point: 248-249 °C
• Boiling Point: 909.1±65.0 °C(Predicted)
• PKA: 7.75±0.25(Predicted)
• PSA: 197.37000
• Density: 1.90±0.1 g/cm3(Predicted)
• LogP: 2.23320
• 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

(+)-Gallocatechingallate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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

Technology Process of Gallocatechin gallate

There total 49 articles about Gallocatechin 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

epitheaflagallin 3-O-gallate

(-)-(2R,3R)-5,7-bis(hydroxy)-2-(3,4,5-tris(hydroxy)phenyl)chroman-3-yl-(3,5-bisbenzyloxy-4-methoxy)benzoate

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.