4''-Methylepigallocatechin gallate

Base Information

• Chemical Name: 4''-Methylepigallocatechin gallate
• CAS No.: 224434-07-5
• Molecular Formula: C₂₃H₂₀O₁₁
• Molecular Weight: 472.405
• NSC Number: 714028
• UNII: CUX41G3911
• DSSTox Substance ID: DTXSID401274844
• Nikkaji Number: J1.051.525D
• Wikidata: Q27275816
• Metabolomics Workbench ID: 48975
• ChEMBL ID: CHEMBL559294
• Mol file: 224434-07-5.mol

Synonyms:224434-07-5;4''-Methylepigallocatechin gallate;Egcg4''me;Epigallocatechin-3-O-(4-O-methyl)gallate;UNII-CUX41G3911;CHEMBL559294;(-)-Epigallocatechin 3-(4-methyl-gallate);[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,5-dihydroxy-4-methoxybenzoate;(-)-Epigallocatechin 3-(4''-O-methyl) gallate;4''-O-Methyl-(-)-epigallocatechin-3-o-gallate;CUX41G3911;(-)-Gallocatechin 3-(4''-O-methyl)gallate;(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,5-dihydroxy-4-methoxybenzoate;Benzoic acid, 3,5-dihydroxy-4-methoxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester;NSC714028;(-)-EPIGALLOCATECHIN 3-(4''-O-METHYL)GALLATE;4"-O-methyl-EGCG;SCHEMBL16887923;CHEBI:191669;4-O-Methylgalloyl epigallocatechin;DTXSID401274844;BDBM50296235;Epigallocatechin 3-(4-methylgallate);NSC-714028;Epigallocatechin 3-O-(4-methylgallate);3-O-(4-O-Methylgalloyl)epigallocatechin;NCI60_039612;4"-Methyl-(-)-epigallocatechin 3-gallate;4''-O-Methylepigallocatechin 3-O-gallate;(-)-Epigallocatechin-3-(4''''-O-methyl)gallate;Q27275816;(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,5-dihydroxy-4-methoxybenzoate

Chemical Property of 4''-Methylepigallocatechin gallate

Chemical Property:

• Melting Point: 226-228 °C (decomp)
• Boiling Point: 879.0±65.0 °C(Predicted)
• PKA: 8.55±0.15(Predicted)
• PSA: 186.37000
• Density: 1.77±0.1 g/cm3(Predicted)
• LogP: 2.53620
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 472.10056145
• Heavy Atom Count: 34
• Complexity: 682

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1O)C(=O)OC2CC3=C(C=C(C=C3OC2C4=CC(=C(C(=C4)O)O)O)O)O)O
• Isomeric SMILES: COC1=C(C=C(C=C1O)C(=O)O[C@@H]2CC3=C(C=C(C=C3O[C@@H]2C4=CC(=C(C(=C4)O)O)O)O)O)O

Technology Process of 4''-Methylepigallocatechin gallate

There total 19 articles about 4''-Methylepigallocatechin 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: 89.0%

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4',5'-tris(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate (901125-32-4) → (-)-(2R,3R)-5,7-bis(hydroxy)-2-(3,4,5-tris(hydroxy)phenyl)chroman-3-yl-(3,5-bisbenzyloxy-4-methoxy)benzoate (224434-07-5)

Guidance literature:

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

DOI:10.1016/j.tet.2006.04.010

Reference yield: 81.0%

5-(2R,3R)-5,7-bis(2-nitrophenylsulfonyloxy)-2-(3,4,5-tris(2-nitrophenylsulfonyloxy)phenyl)chroman-3-yl 4-methoxy-3,5-bis(2-nitrophenylsulfonyloxy)benzoate (1186527-13-8) → (-)-(2R,3R)-5,7-bis(hydroxy)-2-(3,4,5-tris(hydroxy)phenyl)chroman-3-yl-(3,5-bisbenzyloxy-4-methoxy)benzoate (224434-07-5)

Guidance literature:

With caesium carbonate; thiophenol; In acetonitrile; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2009.05.111

Reference yield: 72.0%

5-((2R,3R)-5,7-diacetoxy-3-((3,5-diacetoxy-4-methoxybenzoyl)oxy)chroman-2-yl)-benzene-1,2,3-triyl triacetate (1004981-53-6) → (-)-(2R,3R)-5,7-bis(hydroxy)-2-(3,4,5-tris(hydroxy)phenyl)chroman-3-yl-(3,5-bisbenzyloxy-4-methoxy)benzoate (224434-07-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 6h;

DOI:10.1080/00397911.2016.1278233

upstream raw materials:

S-adenosyl-L-methionine

(-)-epigallocathechin gallate

methyl iodide

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4',5'-tris(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate