Procyanidin B5

Base Information

• Chemical Name: Procyanidin B5
• CAS No.: 12798-57-1
• Molecular Formula: C30H26 O12
• Molecular Weight: 578.529
• UNII: W51N19H6K6
• DSSTox Substance ID: DTXSID00155761
• Nikkaji Number: J257.846H
• Wikipedia: Procyanidin_B5
• Wikidata: Q7247557
• Metabolomics Workbench ID: 140365
• ChEMBL ID: CHEMBL506487
• Mol file: 12798-57-1.mol

Synonyms:procyanidin B5

Chemical Property of Procyanidin B5

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1009.6°C at 760 mmHg
• Flash Point: 564.4°C
• PSA: 220.76000
• Density: 1.705g/cm³
• LogP: 2.99500
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 578.14242626
• Heavy Atom Count: 42
• Complexity: 925

Purity/Quality:

99%, ^*data from raw suppliers

PROCYANIDINB5 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=C1C(=C(C(=C2)O)C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• Isomeric SMILES: C1[C@H]([C@H](OC2=C1C(=C(C(=C2)O)[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• Uses: Procyanidin B5 is a bioactive metabolite extracted from Quercus robur L. leaves/stem bark with antioxidant and antidiabetic properties.

Technology Process of Procyanidin B5

There total 20 articles about Procyanidin B5 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: 100.0%

C93H15(2)H63BrClO12 (1438268-60-0) → [4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin (12798-57-1,12798-58-2,12798-59-3,12798-60-6,88314-65-2,99685-01-5,109582-68-5,109582-69-6,109582-70-9,121842-81-7,123051-09-2)

Guidance literature:

C₉₃H₁₅⁽²⁾H₆₃BrClO₁₂; With 5 % Pd(OH)2 on carbon; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 2.5h;

With hydrogen; triethylamine; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;

DOI:10.1039/c3cc41993b

Reference yield: 66.0%

C86H46(2)H28O12 → [4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin (12798-57-1,12798-58-2,12798-59-3,12798-60-6,88314-65-2,99685-01-5,109582-68-5,109582-69-6,109582-70-9,121842-81-7,123051-09-2)

Guidance literature:

With 5% Pd(OH)₂/C; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 2h;

DOI:10.1039/c4cc06390b

Reference yield: 65.0%

[4,6]-2,3-trans-3,4-trans-2',3,5,7-tetra-O-benzyl-2''',3''',7”-tri(t-butyldimethylsilyloxy)-(+)-catechin-(+)-catechin → [4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin (12798-57-1,12798-58-2,12798-59-3,12798-60-6,88314-65-2,99685-01-5,109582-68-5,109582-69-6,109582-70-9,121842-81-7,123051-09-2)

Guidance literature:

[4,6]-2,3-trans-3,4-trans-2',3,5,7-tetra-O-benzyl-2''',3''',7”-tri(t-butyldimethylsilyloxy)-(+)-catechin-(+)-catechin; With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

With 20% palladium hydroxide-activated charcoal; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 12h; stereoselective reaction; Inert atmosphere;

DOI:10.3390/molecules23010205

upstream raw materials:

(+)-leucocyanidin

catechin

taxifolin

2,3-trans-flavan-3,4-diol

Downstream raw materials:

4β-benzylthioepicatechin

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

(2R,3S,4S,2'R,3'R)-2,2'-Bis-(3,4-dimethoxy-phenyl)-5,7,5',7'-tetramethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,3'-diol

Acetic acid (2R,3R,4R,2'R,3'R)-5,7,3',5',7'-pentaacetoxy-2,2'-bis-(3,4-diacetoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3-yl ester