(-)-Gallocatechin gallate

Base Information

• Chemical Name: (-)-Gallocatechin gallate
• CAS No.: 4233-96-9
• Molecular Formula: C₂₂H₁₈O₁₁
• Molecular Weight: 458.378
• Hs Code.: 29329990
• UNII: IRW3C4Y31Q
• DSSTox Substance ID: DTXSID20195144
• Nikkaji Number: J277.683I
• Wikidata: Q27166763
• Pharos Ligand ID: 8G9CMPPPMGQM
• Metabolomics Workbench ID: 129915
• ChEMBL ID: CHEMBL264938
• Mol file: 4233-96-9.mol

Synonyms:(-)-Gallocatechin gallate;4233-96-9;(-)-Gallocatechol gallate;(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate;Gallocatechin gallate, (-)-;(-)-gallocatechin-3-O-gallate;Gallocatechol, 3-gallate, (-)-;(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate);[(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate;UNII-IRW3C4Y31Q;IRW3C4Y31Q;(-)-Gallocatechin 3-gallate;CCRIS 9286;CHEMBL264938;Benzoic acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2S-trans)-;(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate;GCG;(-)-Gallocatechin 3-O-gallate;Gallocatechin gallate (Gcg);C22-H18-O11;MFCD00214298;L-GCG;D07KXK;Gallocatechingallate(-GCG);ent-Gallocatechin 3-gallate;SCHEMBL49461;NVP-XAA 225;CHEBI:95002;DTXSID20195144;CHEBI:156271;HY-N0522;BDBM50236531;s9058;AKOS015901852;AC-6044;CCG-269313;CS-7698;NCGC00390250-01;BS-50638;LS-38400;(-)-Gallocatechin gallate, analytical standard;Q-100471;BRD-K19216856-001-01-9;Q27166763;(-)-Gallocatechin gallate, from green tea, >=98% (HPLC);(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl3,4,5-trihydroxybenzoate;(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate;BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2S,3R)-3,4-DIHYDRO-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-2H-1-BENZOPYRAN-3-YL ESTER

Chemical Property of (-)-Gallocatechin gallate

Chemical Property:

• Vapor Pressure: 3.71E-35mmHg at 25°C
• Refractive Index: 1.857
• 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.: DMSO (Slightly), Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

Gallocatechin gallate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-26/36

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
• Uses: (-)-Gallocatechin Gallate is a catechins found in green tea that has shown to suppress the activity of cytochrome P 450 1A1.

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:

3,4,5-Trihydroxy-benzoic acid (R)-2-benzylsulfanyl-1-(2,4,6-trihydroxy-benzyl)-2-(3,4,5-trihydroxy-phenyl)-ethyl ester

(2R,3S)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl 3,4,5-trimethoxybenzoate

3,4,5-trihydroxybenzoic acid

LDN-0096568

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.